Crystallochemistry laboratory

Chemistry Department, Warsaw University

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Prof. dr hab. Michał Ksawery Cyrański

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Prof. dr hab. Michał Ksawery Cyrański
Curriculum Vitae
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Scientific interest:

  • Structural chemistry of small organic compounds, cyclic π-electron systems;
  • carbohydrates, supramolecular chemistry with use of boronic acids and pholoroglucinols, chemical crystallography;
  • substituent effect, molecular modeling, quantum-mechanical calculations (ab initio);
  • structural and energetic aspects of aromatic character of π-electron systems;
  • relation between strain and aromaticity, definition of aromaticity

Hobby:

  • Classical music, especially by J. S. Bach,
  • singing in a professional choir.

Phone: +48 22 5526360

Fax: +48 22 8222892

E-Mail: This e-mail address is being protected from spambots. You need JavaScript enabled to view it


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Employment

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1999 -  Professor assistant at the Department of Chemistry , University of Warsaw, Warsaw, Poland.

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2001 - Senior lecturer at the Department of Chemistry, University of Warsaw, Warsaw, Poland.

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Awards and Distinctions

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1997 Reward of the Foundation for Polish Science

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1999 The Włodzimierz Kołos Reward for the best Ph. D. work, Department of Chemistry of Warsaw University, Warsaw, Poland.

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2000 The Antoni Grabowski Reward of an outstanding activity in physical organic and theoretical chemistry, Department of Chemistry of Warsaw University.

2001 The Wiktor Kemula Reward, the Polish Chemical Society, Poland

2001 The Polityka weekly and PKN Orlen, Reward.

2004 The Wiktor Kemula Award, Faculty of Chemistry, University of Warsaw.

2005 - 2007 Stipends from the Rector of the University of Warsaw for Scientific Activity.

2007 Tetrahedron's 'Most Cited Paper' 2003-2006 Award.

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2010 - Award for Distinguished Teaching, Faculty of Chemistry, University of Warsaw.

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Languages

  • polish - mother tongue

  • english - fluent

  • russian - advanced

  • french - advanced

  • czech - advanced

Memberships and Scientific Community Service

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1993 - Member of the Polish Chemical Society.

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1996 - 1997 Elected member of the Warsaw Committee of the Polish Chemical Society.

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1998 - 2000 Elected secretary of the Executive Committee of the Polish Chemical Society.

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2004 - 2006 Elected member of the Warsaw Committee of the Polish Chemical Society.

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2007 Faculty coordinator of abroad practices (LLP Erasmus Program).

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2008 - Member of the disciplinary committee for students, University of Warsaw.

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2008 - Member of the Council concerning post-graduate studies, Faculty of Chemistry, University of Warsaw.

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2009 - Member of the Board "Modern University - a comprehensive program of support for doctoral students and teaching staff of the University of Warsaw", nominated by Rector Magnificus of the University of Warsaw.

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2009 - Elected Member of the Board of Audit of the Polish Chemical Society.

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Organization of conferences and symposia

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2005 - II Warsaw Seminar for PhD students, Chemsession’05, 13.05.2005, Member of the Organizing Committee.

2006 - XVIII International Conference on Physical Organic Chemistry, 20-25.08.2006, Warsaw, Poland, Member of the Organizing Committee.

2009 - VI Warsaw Seminar for PhD students, Chemsession’09, 15.05.2009, Member of the Organizing Committee.

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Research Grants and Fellowships

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1995 - Grant of the State Committee for Scientific Research: 3T09A 061 09, „Structural Investigations of the Aromatic Character of Cyclic π-Electron Systems Containing Nitrogen”.

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1997 - Grant of the State Committee for Scientific Research: 3T09A 019, „Analysis of the Aromatic Character of π-Electron Systems by Separating Geometric and Energetic Contributions”.

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1999 - Grant „Estimating of the Resonance Energy of π-Electron Systems Containing CC Bonds, based on molecular geometry”, Faculty of Chemistry, University of Warsaw: BW-1453/19/99.

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1999 - Deutscher Akademischer Austauschdienst (DAAD) fellowship.

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2000 - Grant „Analysis of the Substituent Effect in Fulvene Derivatives”, Faculty of Chemistry, University of Warsaw: BW-1453/19/2000.

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2000-2002 British-Polish Joint Collaboration Programme KBN and British Council: WAR/341/188, „Joint Experimental/Theoretical Studies in Chemistry” (dr M. K. Cyrański – Polish leader, dr S. T. Howard (Cardiff, UK) – British leader).

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2001 - Grant „Aromatic Character of the Heterocyclic Bases of DNA and RNA”, Faculty of Chemistry, University of Warsaw: BW-1522/19/2001.

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2004 - Grant „Synthesis and structural investigations of selected per-substituted naphthalenes”, Faculty of Chemistry, University of Warsaw: 501/68-BW-1637/02/04.

2005 - Grant „Experimental and Theoretical Investigations of Interactions between Phenylboronic Acids and Aminoacids, University of Warsaw: 501/68-BW-1681/02/05.

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2006 - Grant „Pi-electron Stabilization, Strain Energy, X-ray Diffraction Investigations of (n) [1.7]pyrenophanes, Faculty of Chemistry, University of Warsaw: 501/68-BW-172104.

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2005 - 2007 Grant of the Ministry of Science and Higher Education T09A 031 28, T. M. Krygowski (leader), Studies on unique method of estimation of substituent effects and their interpretation in the frame of electron delocalization.

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2007 - 2009 Grant of the Ministry of Science and Higher Education MNiSW N204 01932/0614, A. Sporzyński, Warsaw University of Technology (leader), Synthesis and structural investigations of arylboronic acids with active functional groups.

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2010 - 2013 Grant of the Ministry of Science and Higher Education MNiSW N N204 177639, S. Witkowski, University of Bialystok (leader), Experimental and theoretical correlation structure of vitamin E and its derivatives with chiral-optical properties.

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2011 - 2012 Grant of the Fund of Polish Science and Technology by the Ministry of Science and Higher Education 614/FNiTP/115/2011 (Leader), Purchase of equipment allowing for advanced research in the physical and chemical engineering to obtain crystalline, structural characterization and analysis of crystal hydrates and clathrates of gases and/or other chemicals, as well as studies of biologically active substances using a unique on a world scale in situ crystallization method.


Oryginal papers

  1. R. Anulewicz, T. Bąk, M. Cyrański, T. M. Krygowski, D. Rasała, B. Świrska, „Substituent Effect on Pyridine and Benzene Rings in Some 4-aryl-2,6-diphenylpiridines. Crystal and Molecular Structure of Methyl - and Fluoro Derivatives”, Pol. J. Chem., 69, 597-604 (1995).

  2. M. Cyrański, T. M. Krygowski, „Structural Studies of Disubstituted Benzene Derivatives. Part I. Factor Analysis Study of the Molecular Geometry in Para-disubstituted Benzene Derivatives”, Pol. J. Chem., 69, 1080-1087 (1995).

  3. M. Cyrański, T. M. Krygowski, „Structural Studies of Disubstituted Benzene Derivatives. Part II. Factor and Regression Analyses of Aromaticity of the Ring in Para-disubstituted Benzene Derivatives”, Pol. J. Chem., 69, 1088-1096 (1995).

  4. R. Anulewicz, T. Bąk, M. Cyrański, T. M. Krygowski, D. Pawlak, B. Pniewska, D. Rasała, R. Gawinecki, „Substituent Effect on the Geometry of the Pyridine Ring in 1-methyl-4-(-4-R-phenyl)-2,6-diphenylpyridinium Perchlorates”, Acta Chem. Scand., 49, 515-523 (1995).

  5. T. M. Krygowski, A. Ciesielski, M. Cyrański, „Aromatic Character and Energy of the Five- and Seven-membered Rings in Derivatives of Penta- and Heptafulvene Substituted in Exocyclic Position”, Chem. Papers, 49, 128-132 (1995).

  6. T. M. Krygowski, A. Ciesielski, M. Cyrański, „Aromatic Character of the Cyclopentadienyl Moiety Embedded in Various Chemical Environments: a Statistical Treatment of the Structural Data”, J. Mol. Struct., 374, 277-290 (1996).

  7. T. M. Krygowski, M. Cyrański, „Separation of the Energetic and Geometric Contributions to the Aromaticity of π-electron Carbocyclics”, Tetrahedron, 52, 1713-1722 (1996).

  8. T. M. Krygowski, M. Cyrański, A. Ciesielski, B. Świrska, P. Leszczyński, „Separation of the Energetic and Geometric Contributions to the Aromaticity. 2. Analysis of the Aromatic Character of Benzene Rings in Their Various Topological Environments in the Benzenoid Hydrocarbons. Crystal and Molecular Structure of Coronene”, J. Chem. Inf. Comput. Sci., 36, 1135-1141 (1996).

  9. M. Cyrański, T. M. Krygowski, „Separation of the Energetic and Geometric Contributions to the Aromaticity. 3. Analysis of the Aromatic Character of Benzene Rings in Their Various Topological and Chemical Environments in the Substituted Benzene Derivatives”, J. Chem. Inf. Comput. Sci., 36, 1142-1145 (1996).

  10. T. M. Krygowski, M. Cyrański, „Separation of the Energetic and Geometric Contributions to the Aromaticity. Part IV. A General Model for the π-Electron Systems”, Tetrahedron, 52, 10255-10264 (1996).

  11. M. Cyrański, T. M. Krygowski, „Separation of the Energetic and Geometric Contributions to the Aromaticity of π-electron Carbocyclics. Part V. Analysis of the Aromatic Character of Aza-analogues of Benzenoid Hydrocarbons”, Tetrahedron, 52, 13795-13802 (1996).

  12. T. M. Krygowski, M. Cyrański, M. Wisiorowski, „Through Space Substituent Effects Shedding Light on Aromaticity. Energetic and Geometric Contributions to Aromaticity”, Pol. J. Chem., 70, 1351-1356 (1996).

  13. T. M. Krygowski, M. K. Cyrański, K. Nakata, M. Fujio, Y. Tsuno, „Separation of the Energetic and Geometric Contributions to the Aromaticity. Part VI. Changes in Aromatic Character of the Rings in Napthalene, Anthracene, Phenanthrene and Pyrene Derivatives Induced by the Charged Substituent CH2+”, Tetrahedron, 53, 11383-11398 (1997).

  14. T. M. Krygowski, M. K. Cyrański, K. Nakata, M. Fujio, Y. Tsuno, „Separation of the Energetic and Geometric Contributions to Aromaticity. Part VII. Changes of the Aromatic Character of the Rings in Naphthalene Induced by the Charged Substituent CH2+. The Dependence on the Position of the Substitution, Torsion Angle and the Exocyclic Bond Length Variation”, Tetrahedron, 54, 3303-3310 (1998).

  15. M. K. Cyrański, T. M. Krygowski, M. Wisiorowski, N. J. R. van Eikema Hommes, P. v R. Schleyer, „Global and Local Aromaticity in Porphyrins: An Analysis Based on Molecular Geometries and Nucleus-Independent Chemical Shifts”, Angew. Chem. Int. Ed., 37, 177-180 (1998); Angew. Chem., 110, 187- 190 (1998).

  16. Jarmuła, R. Anulewicz, A. Leś, M. K. Cyrański, L. Adamowicz, M. Bretner, K. Felczak, T. Kulikowski, T. M. Krygowski, W. Rode, „Crystal Structures of 5-fluoro-dUrd and its 2 and/or 4-thio Analogues: Models of Substituted dUMP Pyrimidine Ring Interacting with Thymidylate Synthase”, BBA – Protein Structure & Molecular Enzymology, 1382/2, 277-286 (1998).

  17. M. K. Cyrański, T. M. Krygowski, C. W. Bird, „Separation of the Energetic and Geometric Contributions to Aromaticity. Part VIII. Changes in Aromaticity and the Evidence for the Multi-Dimensionality of the Aromatic Character of Benzene Rings in Para- and Meta-Cyclophanes”, Tetrahedron, 54, 9711-9720 (1998).

  18. A. Jarmuła, M. K. Cyrański, A. Leś, T. M. Krygowski, W. Rode, „Interaction of Thymidylate Synthase with 5-Fluoro-Substituted DUMP Analogues in View of the Pyrimidine Ring Structure”, Pol. J. Chem., 72, 1958-1962 (1998).

  19. T. M. Krygowski, R. Anulewicz, M. K. Cyrański, A. Puchała, D. Rasała, „Separation of the Energetic and Geometric Contributions to Aromaticity. Part IX. Aromaticity of Pyrazoles in Dependence on the Kind of Substitution”, Tetrahedron, 54, 12295-12300 (1998).

  20. M. K. Cyrański, J. Mieczkowski, „2-Chloro-3-cyano-6-phenylpyridine”, Acta Cryst., C54, 1521-1523 (1998).

  21. T. M. Krygowski, E. Piętka, R. Anulewicz, M. K. Cyrański, J. Nowacki, „Angular Group Induced Bond Alternation. III. The Case of o-Dimethoxybenzene Derivatives. Crystal and Molecular Structure of 3,4-dimethoxybenzaldehyde[(4-metylphenyl)sulphonyl]-hydrazone”, Tetrahedron, 54, 12289-12294 (1998).

  22. D. Madura, T. M. Krygowski, M. K. Cyrański, „Structural Aspects of the Aromaticity of Cyclic π-electron Systems with BN Bonds”, Tetrahedron, 54, 14913-14918 (1998).

  23. M. K. Cyrański, T. M. Krygowski, „Separation of the Energetic and Geometric Contributions to Aromaticity. Part X. The Case of Benzene Rings in Benzenoid Hydrocarbons”, Tetrahedron, 54, 14919-14924 (1998).

  24. P. Mičúch, L. Fišera, M. K. Cyrański, T. M. Krygowski, „Reversal of Stereoselectivity of Mg(II) Catalysed 1,3-Dipolar Cycloaddition. Effect of Microwave Irradiation to Reaction Site”, Tetrahedron Lett., 40, 167-170 (1999).

  25. M. K. Cyrański, T. M. Krygowski, „Two Sources of Decrease of Aromaticity: Bond Length Alternation and Bond Elongation. Part I. An Analysis Based on Benzene Ring Deformations”, Tetrahedron, 55, 6205-6210 (1999).

  26. T. M. Krygowski, M. K. Cyrański, „Two Sources of the Decrease of Aromaticity: Bond Length and Bond Elongation. Part II. An Analysis Based on Geometry of the Singlet and Triplet States of 4nπ Annulenes: C4H4, C5H5+, C6H62+, C7H7-, C9H9+”, Tetrahedron, 55, 11143-11148 (1999).

  27. R. Anulewicz-Ostrowska, T. M. Krygowski, M. K. Cyrański, M. P. Matuszewska, „Crystal and Molecular Structure of 1,3,5-Trimethoxy-2,4,6-trinitrobenzene. Mesomeric Effects for Out-of-plane Twisted Substituents” Pol. J. Chem. 73, 1895-1901 (1999).

  28. T. M. Krygowski, B. Stępień, R. Anulewicz-Ostrowska, M. K. Cyrański, S. J. Grabowski, Z. Rozwadowski, T. Dziembowska, „Crystal and molecular structure of N-(3,5-dichloro-2-hydroxybenzylidene)- and N-(2-hydroxy-3-methoxybenzylidene)-aniline oxides. Delocalization in the spacer of the intramolecular H-bond and the problem of quasi-aromaticity”, Collect. Czech. Chem. Commun. 64, 1797-1806 (1999).

  29. R. Sleziak, A. Krutošíková, M. K. Cyrański, T. M. Krygowski, „Furo[2,3-b]pyrrole Derivatives. Syntheses and Reactions in the Furan and Pyrrole Ring” Pol. J. Chem., 74, 207-217 (2000).

  30. Matraszek, J. Mieczkowski, M. K. Cyrański, „Synthesis of Crotonoyl, Cynamoyl and p-Methoxycynamoyl Derivatives of Camphoric Imide. Crystal and Molecular Structure of (1R, 5S)-3-[(E)-2’-butenoyl}-1,8,8-trimethyl-3-azabicyclo [3.2.1]octane-2,4-dione” Pol. J. Chem. 74, 477-482 (2000).

  31. P. Mičúch, L. Fišera, M. K. Cyrański, T. M. Krygowski, J. Krajčík, „Reversal of Diastereoselectivity of Nitrile Oxide 1,3-Dipolar Cycloadditions by Mg(II). Acceleration of Cycloaddition by Microwave Irradiation”, Tetrahedron, 56, 5465-5472 (2000).

  32. T. M. Krygowski, E. Pindelska, M. K. Cyrański, S. J. Grabowski, „Angular Group Induced Bond Alternation (AGIBA). Part 4. Does the Effect Operate in the Systems with Alternated Bonds?” Tetrahedron, 56, 8715-8719 (2000).

  33. M. K. Cyrański, B. T. Stępień, T. M. Krygowski, „Global and Local Aromaticity of Linear and Angular Polyacenes”, Tetrahedron, 56, 9663-9667 (2000).

  34. S. T. Howard, M. K. Cyrański, L. Z. Stolarczyk, “On the Calculation of Bond Energies from Atomisation Energies”, Chem. Comm., 197-198 (2001).

  35. E. Bednarek, B. Modzelewska-Banachiewicz, M. K. Cyrański, J. Sitkowski, I. Wawer, „The 1H NMR, 13C and 15N NMR Study on 5-carboxymethyl-1,2,4-triazole and 5-oxo-1,2,4-triazine derivatives”, J. Mol. Struct. 562/1-3 167-175 (2001).

  36. M. K. Cyrański, I. Wawer, A. Zielińska, A. Mrozek, V. Koleva, C. Lozanova, „Structural Studies of 1-(2-Hydroxy-4-Bromophenyl)-4-Methyl-4-Imidazoline-2-One”, J. Phys. Org. Chem., 14,323-327 (2001).

  37. M. K. Cyrański, T. M. Krygowski, A. Krutošíková, R. Sleziak, „Aromaticity of Dihetero Analogues of Pentalene Dianion. X-ray and ab initio Studies of Eight Methyl Furo[3,2-b]pyrrole-5-carboxylate Derivatives and Five Methyl Furo[2,3-b]pyrrole-5-carboxylate Derivatives, Tetrahedron, 57 8867-8873 (2001).

  38. E. Pindelska, T. M. Krygowski, R. Anulewicz-Ostrowska, M. K. Cyrański, J. Nowacki, „Angular Group Induced Bond Alternation (AGIBA). Part VI – Competition Between the AGIBA and Through Resonance Effects, J. Phys. Org. Chem., 14, 764-769 (2001).

  39. B. T. Stępień, M. K. Cyrański, T. M. Krygowski, „Aromaticity Strongly Affected by Substituents in Fulvene and Heptafulvene as a New Method of Estimating the Resonance Effect” Chem. Phys. Lett. 350, 537-542 (2001).

  40. T. M. Krygowski, M. K. Cyrański, R. Anulewicz-Ostrowska, „Guanidinium Cation – An Acyclic Analogue of Benzene?” Pol. J. Chem., 75, 1939-1942 (2001).

  41. M. K. Cyrański, T. M. Krygowski, A. R. Katritzky, P. v. R. Schleyer, „To What Extent Can Aromaticity Be Defined Uniquely?” J. Org. Chem. 67, 1333-1338 (2002).

  42. R. Fischer, A. Drucková, L. Fišera, A. Rybár, Ch. Hametner, M. K. Cyrański, „New Chiral Nitrones in the Synthesis of Modified Nucleosides” Synlett 7, 1113-1117 (2002).

  43. T. M. Krygowski, E. Pindelska, M. K. Cyrański, G. Häfelinger, „Planarization of 1,3,5,7-cyclooctatetraene as a Result of a Partial Rehybridization at Carbon Atoms: an MP2/6-31G* and B3LYP/6-311G** Study” Chem. Phys. Lett. 359, 158-163 (2002).

  44. B. T. Stepień, T. M. Krygowski, M. K. Cyrański, „Extent of Cyclic π-Electron Delocalization Modification in Exocyclically Substituted Fulvenes” J. Org. Chem. 67, 5987-5992 (2002).

  45. T. M. Krygowski, E. Pindelska, M. K. Cyrański, J. Nowacki, „Angular Group Induced Bond Alternation (AGIBA) Part IX. Interactions with the Pirimidine Ring” Int. Electr. J. Mol. Des., 1, 593-602 (2002).

  46. M. K. Cyrański, P. v. R. Schleyer, T. M. Krygowski, H. Jiao, G. Hohlneicher, „Facts and Artifacts about Aromatic Stability Estimation”, Tetrahedron, 59, 1657-1665 (2003).

  47. G. J. Bodwell, J. N. Bridson, M. K. Cyrański, J. W. J. Kennedy, T. M. Krygowski, M. R. Mannion, D. O. Miller, „Nonplanar Aromatic Compounds. 8. Synthesis, Crystal; Structures and Aromaticity Investigations of the 1,n-Dioxa[n](2,7)pyrenophanes. How does Bending Affect the Cyclic π-Electron Delocalization of the Pyrene Systems?”, J. Org. Chem. 68, 2089-2098 (2003).

  48. I. Blanáriková-Hlobilová, Z. Kubánová, L. Fišera, M. K. Cyrański, P. Salanski, J. Jurczak, N. Prónayova, “Stereoselectivity of 1,3-dipolar Cycloadditions of L-valine-derived Nitrones with Methyl Acrylate” Tetrahedron, 59, 3333-3339 (2003).

  49. B. T. Stępień, T. M. Krygowski, M. K. Cyrański, „Variation of the π-Electron Delocalisation in Exocyclically Substituted Heptafulvene Derivatives” J. Phys. Org. Chem., 16, 426-430 (2003).

  50. E. D. Raczyńska, M. Darowska, M. K. Cyrański, M. Makowski, T. Rudka, J. F. Gal, P. C. Maria, „Ab initio study of Tautomerism and of Basicity Center Preference in Histamine, from gas phase to solution – comparison with experimental data (gas phase, solution, solid state)” J. Phys. Org. Chem., 16, 783-796 (2003).

  51. M. K. Cyrański, M. Gilski, M. Jaskólski, T. M. Krygowski, „On the Aromatic Character of Heterocyclic Bases of DNA and RNA”, J. Org. Chem., 68, 8607-8613, (2003).

  52. R. Fischer, E. Hýrošová, A. Drucková, L. Fišera, C. Hametner, M. K. Cyrański, „Isoxazolinyl Spironucleosides: Stereoselectivity of 1,3-Dipolar Cycloadditions of 7-Methylenepyrrolo[1,2-c]pyrimidin-1(5H)-ones”, Synlett, 15, 2364-2368 (2003).

  53. B. T. Stępień, T. M. Krygowski, M. K. Cyrański, J. Młochowski, P. Orioli, F. Abbate, „How Far is the pi-Electron Delocalization of the Phenanthrene Moiety Modified in the Aza-Analogues and Their N-oxides?” Arkivoc, vi, 185-201 (2004).

  54. B. Dugovic, L. Fišera, C. Hametner, M. K. Cyrański, N. Prónayová, “Diastereoselectivity of Chiral Nitrone 1,2-Dipolar Cycloaddition to Baylis-Hillman Adducts”, Monatshefte, 135, 685-696 (2004).

  55. T. M. Krygowski, M. K. Cyrański, D. D. Sung, B. T. Stępień, „Sololysis of aromatic benzoyl chlorides: how is the pi-electron stabilization of the aromatic acyl chlorides and acylium cations related to the pi-electron delocalization?”, J. Phys. Org. Chem., 17, 699-706 (2004).

  56. M. K. Cyrański, J. Frelek, I. Jastrzębska, J. W. Morzycki, „Rearrangement of 23-oxospirostanes to the 22-oxo-23-spiroketal isomers promoted by Lewis acids – X-ray crystal structure of (23R,25S)-3b-acetoxy-16b,23:23,26-diepoxy-5b-cholestan-22-one”, Steroids, 69, 395-400 (2004).

  57. T. M. Krygowski, K. Ejsmont, B. T. Stępień, M. K. Cyrański, J. Poater, M. Sola, "Relation between the Substituent Effect and Aromaticity", J. Org. Chem., 69, 6634-6640 (2004).

  58. M. K. Cyrański, S. T. Howard, M. L. Chodkiewicz, "Bond energy, aromatic stabilization energy and strain in IPR fullerenes", Chem Comm., 2458-2459, (2004).

  59. P. Micuch, L. Fišera, M.K. Cyrański "Reversal of Diastereoselectivity of Mesitonitrile Oxide 1,3-Dipolar Cycloadditions with Penta-1,4-diene-3-ol by Mg(II)", Pol. J. Chem., 79, 65-72 (2005).

  60. T. M. Krygowski, B. T. Stępień, M. K. Cyrański, "How the Substituent Effect Influences pi-Electron Delocalisation in the Ring of Reactants in the Reaction Defining the Hammett Substituent Constants σm and σp", Int. J. Mol. Sci., 6, 45-51 (2005)

  61. A. Temeriusz, T. Gubica, P. Rogowska, K. Paradowska, M. K. Cyrański, Crystal structure and solid state 13C NMR analysis of nitrophenyl 2,3,4,6-tetra-O-acetyl-b-D-gluco- and D-galactopyranosides, Carbohydr. Res.340, 1175-1184 (2005).

  62. B. Dugović, L. Fisera, M. K. Cyrański, C. Hametner, N. Prónayová, M. Obranec, Reversal of Regioselectivity of Nitrone Cycloadditions by Lewis Acids, Helv. Chim. Acta, 88, 1432-1443 (2005).

  63. T. M. Krygowski, B. T. Stępień, M. K. Cyrański, K. Ejsmont, Relation between Resonance Energy and Substituent Resonance Effect in p-Phenols, J. Phys. Org. Chem., 18, 886-891 (2005).

  64. A. Sporzyński, M. Lewandowski, P. Rogowska, M. K. Cyrański, "1,3-Dihydro-1-hydroxy-3-morpholin-4-yl-2,1-benzoxaborole: Product of the Reaction of o-Formylphenylboronic Acid with Morpholine", Appl. Organomet. Chem., 19, 1202-1203 (2005).

  65. R. Fischer, E. Hyrosova, L. Fisera, C. Hametner, M. K. Cyranski, "Preparation of 7-Methylenepyrrolo[1,2-c]pyrimidin-1(5H)-ones and their 1,3-Dipolar Cycloadditions towards Isoxazolinyl and Isoxazolidinyl Spironucleosides", Chem. Pap., 59, 275-288 (2005).

  66. A. Temeriusz, M. Rowińska, B. Piekarska-Bartoszewicz, R. Anulewicz-Ostrowska, M. K. Cyrański, Synthesis and Structure of 2-Hydroxy-2-Methyl-1,3-Bis-(Methyl 3,4,6-Tri-O-Acetyl-ß-D-Glucopyranosid-2-yl)-Imidazolidine-4,5-Dione, J. Carbohydr. Chem., 2005, 24, 697 - 704.

  67. A. Temeriusz, T. Gubica, P. Rogowska, K. Paradowska, M. K. Cyrański, "Crystal structure and solid-state 13C NMR analysis of N-p-nitrophenyl-α-D-ribopyranosylamine, N-p-nitrophenyl-α-D-xylopyranosylamine, and solid-state 13C NMR analysis of N-p-nitrophenyl-2,3,4-tri-O-acetyl-β-D-lyxopyranosylamine and N-p-nitrophenyl-2,3,4-tri-O-acetyl-α-L-arabinopyranosylamine", Carbohydr. Res., 340, 2645-2653 (2005)

  68. P. Rogowska, M. K. Cyrański, A. Sporzyński, A. Ciesielski, "Evidence for strong heterodimeric interactions of phenylboronic acids with amino acids", Tetrahedron Letters, 47, 1389-1393 (2006).

  69. A. Temeriusz, T. Gubica, P. Rogowska, K. Paradowska, M. K. Cyranski, "Crystal structure and solid-state 13C NMR analysis of N-o-, N-m- and N-p-nitrophenyl-2,3,4,6-tetra-O-acetyl-b-D-glucopyranosylamines and their N-acetyl derivatives", Carbohydr. Res., 341, 2581-2590 (2006)

  70. A. Ciesielski, M. K. Cyrański, T. M. Krygowski, P. W. Fowler, M. Lillington, "Super-Delocalized Valence Isomer of Coronene", J. Org. Chem., 71, 6840-6845 (2006)

  71. T. M. Krygowski, M. A. Dobrowolski, K. Zborowski, M. K. Cyrański, "Relation between the substituent effect and aromaticity. Part II. The case of meta- and para- homodisubstituted benzene derivatives", J. Phys. Org. Chem., 19, 889-895 (2006)

  72. M. K. Cyrański, R. W. A. Havenith, M. A. Dobrowolski, B. R. Gray, T. M. Krygowski, P. W. Fowler, L. W. Jenneskens, "The Phenalenyl Motif: a Magnetic Chameleon", Chemistry Eur. J., 13, 2201-2207 (2007)

  73. M. A. Dobrowolski, M. K. Cyrański, M. Pisklak, I. Wawer, D. Matosiuk, "Structural Studies of 1-Aryl-2-aminoimidazolinium Bromides: Focus on Tautomer Preference of the 2-Aminoimidazoline Moiety in the Solid State", Pol. J. Chem., 81, 1037-1048 (2007).

  74. B. Zhang, G. P. Manning, M. A. Dobrowolski, M. K. Cyrański, G. J. Bodwell, "Nonplanar Aromatic Compounds. 9. Synthesis, Structure, and Aromaticity of 1:2,13:14-Dibenzo[2]paracyclo[2](2,7)-pyrenophane-1,13-diene", Org. Lett., 10, 273-276 (2008).

  75. W. Ziemkowska, R. Anulewicz-Ostrowska, M. Cyrański, "Synthesis and structural characterisation of alkylaluminium and alkylgallium pinacolates", Polyhedron, 27, 962-968 (2008).

  76. M. K. Cyrański, A. Jezierska, P. Klimentowska, J. J. Panek, G. Z. Żukowska, A. Sporzyński, "Structural and spectroscopic properties of an aliphatic boronic acid studied by combination of experimental and theoretical methods", The Journal of Chemical Physics 2008, 128, 124512.

  77. M. K. Cyranski, A. Jezierska, P. Klimentowska, J. J. Panek, A.Sporzynski "Impact of intermolecular hydrogen bond on structural properties of phenylboronic acid: quantum chemical and X-ray study", J. Phys. Org. Chem. 21, 472-482 (2008)

  78. A. Adamczyk-Wożniak, Z. Brzózka, M. K. Cyrański, A.Filipowicz-Szymanska, P. Klimentowska, A. Żubrowska, K. Żukowski, A. Sporzyński, "ortho-(Aminomethyl)phenylboronic acids - synthesis, structure and sugar receptor Activity", Applied Organometalic Chemistry, 22, 427-432(2008)

  79. A. Ciesielski, T. M. Krygowski, M. K. Cyrański, "Why Are the Kinked Polyacenes More Stable than the Straight Ones? A Topological Study and Introduction of a New Topological Index of Aromaticity", Journal of Chemical Information and Modeling, 48, 1358-1366 (2008)

  80. K. Paradowska, T. Gubica, A. Temeriusz, M. K. Cyrański, I. Wawer, "13C CP MAS NMR and crystal structure of methyl glycopyranosides", Carbohydrate Research, 343, 2299-2307 (2008)

  81. B. T. Fraczak, T. M. Krygowski, M. K. Cyrański, B. Korybut-Daszkiewicz, "Formyl Group as a Source of AGIBA Effect in Mono-, Di- and Tri- Formylo Derivatives of Benzene" Pol. J. Chem., 82, 1999-2007 (2008)

  82. M. A. Dobrowolski, M. K. Cyranski, B. L. Merner, G. J. Bodwell, J. I. Wu, P. v. Rague Schleyer, "Interplay of pi-Electron Delocalization and Strain in [n](2,7)Pyrenophanes", J. Org. Chem., 73, 8001-8009 (2008)

  83. M. A. Dobrowolski, J. Kaniewski, T. M. Krygowski, M. K. Cyranski, "Acyclic versus Cyclic pi-Electron Delocalization. How the Substituent Effect is Related to the pi-Electron Delocalization?", Coll. Czech. Chem. Commun., 74, 115-129 (2009)

  84. A. Adamczyk-Wozniak, M. K. Cyranski, A. Dabrowska, B. Gierczyk, P. Klimentowska, G. Schroeder, A. Zubrowska, A. Sporzynski, "Hydrogen bonds in phenylboronic acids with polyoxaalkyl substituents at ortho-position" J. Mol. Struct. 920, 430-435 (2009)

  85. A. Ciesielski, T. M. Krygowski, M. K. Cyranski, M. A. Dobrowolski, A. T. Balaban, "Are Thermodynamic and Kinetic Stabilities Correlated? A Topological Index of Reactivity toward Electrophiles Used as a Criterion of Aromaticity of Polycyclic Benzenoid Hydrocarbons", J. Chem. Inf. Model., 49, 369-376 (2009)

  86. J. I. Wu, M. A. Dobrowolski, M. K. Cyranski, B. L. Merner, G. J. Bodwell, Y. Mo, P. v. R. Schleyer, "On the Aromatic Stabilization Energy of the 4N pi-electron Pyrene", Mol. Phys., 107, 1177-1186 (2009)

  87. M. A. Dobrowolski, T. M. Krygowski, M. K. Cyranski, "Substituent Constants (sp-) of the Rotated Nitro Group. The Interplay Between the Substituent Effect of a Rotated -NO2 Group and H-Bonds Affecting pi-Electron Delocalization in 4-Nitrophenol and 4-Nitrophenolate Complexes: a B3LYP/6-311+G** Study", Croat. Chem. Acta, 82, 139-147 (2009)

  88. W. Ziemkowska, M. Cyranski, A. Kunicki, "Alkylaluminum Derivatives of Diphenic Acid: Novel Aluminum Carboxylates", Inorg. Chem., 48, 7006-7008 (2009)

  89. T. Gubica, A. Temeriusz, K. Paradowska, A. Ostrowski, P. Klimentowska, M. K. Cyranski, "Single-crystal and powder X-ray diffraction and solid-state 13C NMR of p-nitrophenyl glycopyranosides, the derivatives of D-galactose, D-glucose, and D-mannose", Carbohydrate Research, 344, 1734-1744 (2009)

  90. W. Ziemkowska, M. K. Cyranski, "Synthesis and Structural Characterization of Some Alkylindium Bisphenoxides", Organometallics, 28, 5593-5596 (2009)

  91. A. Ciesielski, T. M. Krygowski, M. K. Cyranski, M. A. Dobrowolski, J.-I. Aihara, "Graph-topological approach to magnetic properties of benzenoid hydrocarbons", Phys. Chem. Chem. Phys. 11, 11447-11455 (2009)

  92. Bharat, R. Bhola, T. Bally, A. Valente, M. K. Cyranski, L. Dobrzycki, S. M. Spain, P. Rempala, M. R. Chin, B. T. King, "Quadrannulene: A Nonclassical Fullerene Fragment", Angew. Chem. Int. Ed., 49, 399 -402 (2010)

  93. A. Adamczyk-Wozniak, M. K. Cyranski, M. Jakubczyk, P. Klimentowska, A. Koll, J. Kolodziejczak, G. Pojmaj, A Zubrowska, G. Z. Zukowska, A. Sporzynski, "Influence of the Substituents on the Structure and Properties of Benzoxaboroles", J. Phys. Chem. A, 114, 2324-2330 (2010)

  94. W. Ziemkowska, Jakub Kochanowski, M. K. Cyranski, "Synthesis, structures and e-caprolactone polymerization activity of aluminum N,N0-dimethyloxalamidates", J. Organomet. Chem., 695, 1205-1209 (2010)

  95. D. T. Gryko, M. K. Rogacki, J. Klajn, M. Gałęzowski, D. K. Stępień, M. K. Cyrański, Unprecedented 1,3-Dipolar Cycloaddition: From 1,4,5,8-Naphthalene Bisimides to a New Heterocyclic Skeleton, Org. Lett. 2010, 12, 2020-2023.

  96. A. Ciesielski, T. M. Krygowski, M. K. Cyrański, How to Find the Fries Structures for Benzenoid Hydrocarbons, Symmetry 2010, 2, 1390-1400.

  97. A. Budzianowski, M. Derzsi, P. J. Leszczyński, M. K. Cyrański, W. Grochala, Structural polymorphism of pyrazinium hydrogen sulfate: extending chemistry of the pyrazinium salts with small anions, Acta Cryst. 2010, B66, 451-457.

  98. A. J. Churchard, M. K. Cyrański, W. Grochala, Hexaaquanickel(II) disulfato(1,4,8,11-tetraazacyclotetradecane)nickelate(II) dihydrate, Acta Cryst. 2010, C66, m263-m265.

  99. J. Cz. Dobrowolski, M. H. Jamróz, R. Kołos, J. E. Rode, M. K. Cyrański, J. Sadlej, IR low-temperature matrix, X-ray and ab initio study on L-isoserine conformations, Phys. Chem. Chem. Phys. 2010, 12, 10818-10830.

  100. E. Megiel, A. Kaim, M. K. Cyrański, Theoretical and experimental studies on stability of the C-ON bond in new ketone functionalized N-alkoxyamines, J. Phys. Org. Chem. 2010, 23, 1146-1154.

  101. A. J. Churchard, M. K. Cyrański, L. Dobrzycki, A. Budzianowski, W. Grochala, Nickel macrocycles with complex hydrides -new avenues for hydrogen storage research, Energy Environ. Sci. 2010, 3, 1973-1978.

  102. W. Ziemkowska, E. Jaśkowska, E. Zygadło-Monikowska, M. K. Cyrański, J. Organomet. Chem. 2010, 2011, 696, 2079-2085.

  103. A. Ciesielski, T. M. Krygowski, M. K. Cyrański, A. T. Balaban, Phys. Chem. Chem. Phys. 2011, 13, 3737-3747.

  104. T. Gubica, D. K. Stępień, A. Temeriusz, K. Paradowska, E. Głowacka, M/ K. Cyrański, A. Ostrowski, Solid-state structure of N-o-, N-m-, and N-p-nitrophenyl-2,3,4-tri-O-acetyl-β-Dxylopyranosylamines, Carbohydrate Research 2011, 346, 2491-2498.

  105. M. Shahamirian, M. K. Cyrański, T. M. Krygowski, Conjugation Paths in Monosubstituted 1,2- and 2,3-Naphthoquinones, J. Phys. Chem. A 2011, 115, 12688-12694

  106. M. A. Dobrowolski, A. Ciesielski, M. K. Cyrański, On the aromatic stabilization of corannulene and coronene, Phys. Chem. Chem. Phys. 2011, 13, 20557-20563.

  107. W. Ziemkowska, P. Żuk, M. K. Cyrański, A. Kunicki, Synthesis and structure of aluminum 2,20-oxobis(phenolate)s, J. Mol. Struct. 2011, 1006, 606-610.

  108. P. J. Leszczyński, A. Budzianowski, Ł. Dobrzycki, M. K. Cyrański, M. Derzsi, W. Grochala, Thermal and chemical decomposition of di(pyrazine)silver(II) peroxydisulfate and unusual crystal structure of a Ag(I) by-product, Dalton Trans. 2012, 41, 396-402. + coverpage.

  109. T. Gubica D. K. Stępień, A. Ostrowski, D. M. Pisklak, A. Temeriusz, E. Głowacka, K. Paradowska, M. K. Cyrański, Crystal and molecular structure of nitrophenyl 2,3,4-tri-O-acetyl-?-D-xylopyranosides J. Mol. Struct. 2011, 1007, 227-234.

  110. W. Grochala, M. K. Cyrański, M. Derzsi, T. Michałowski, P. J. Malinowski, Z. Mazej, D. Kurzydłowski, W. Koźmiński, A. Budzianowski, P. J. Leszczyński, Crystal and electronic structure, lattice dynamics and thermal properties of Ag(I)(SO3)R (R = F, CF3) Lewis acids in the solid state, Dalton Trans. 2012, 41, 2034-2047.

  111. T. M. Krygowski, M. A. Dobrowolski, M. K. Cyrański, W. P. Oziminski, P. Bultinck, Substituent effects in 1,4-disubstituted benzene and cyclohexadiene: Olefinic vs aromatic electron shift pathway of the substituent effect, Computational and Theoretical Chemistry 2012, 984, 36-42.

Reviews

  1. T. M. Krygowski, M. Cyrański, „Aromatic Character of Carbocyclic π-Electron Systems Deduced From Molecular Geometry”, chapter 7, vol. 3 „Advances in Molecular Structure Research” (M. and I. Hargittai Edts), 227-268, JAI press (1997).

  2. T. M. Krygowski, M. K. Cyrański, „Molecular Geometry as a Source of Chemical Information for π-Electron Compounds”, chapter 6; vol. 5 „Theoretical and Computational Chemistry” (C. Párkányi Ed.), 153-187, Elsevier Science B.V. (1998).

  3. T. M. Krygowski, M. K. Cyrański, Z. Czarnocki, G. Häfelinger, A. R. Katritzky, „Aromaticity – A Theoretical Concept of Immense Practical Importance”, Tetrahedron Report, 56, 1783-1796 (2000).

  4. M. K. Cyrański, T. M. Krygowski, „Aromatyczność – Podstawowe Pojęcie Współczesnej Chemii Organicznej”, Wiad. Chem., 54, 357-369 (2000).

  5. M. K. Cyrański, T. M. Krygowski, „Ilościowe Kryteria Aromatyczności”, Wiad. Chem, 54, 533-564 (2000).

  6. E. D. Raczyńska, M. K. Cyrański, M. Darowska, T. Rudka, „Structure and Proton-transfer Reactions in Histamine”, Targets in Heterocyclic Systems, (O. A. Attanasi and D. Spinelli Edts), tom 4, 327-356 (2000).

  7. T. M. Krygowski, M. K. Cyrański, „Structural Aspects of Aromaticity”, Chem. Rev., 101, 1385-1419 (2001).

  8. E. D. Raczyńska, M. K. Cyrański, M. Gutowski, J. Rak, J.-F. Gal, P.-C. Maria, M. Darowska, K. Duczmal, „Consequences of Proton Transfer in Guanidine” J. Phys. Org. Chem., 16, 91-106 (2003).

  9. T. M. Krygowski, M. K. Cyrański, „Angular Group Induced Bond Alternation (AGIBA). A New Kind of Substituent Effect Detected in Molecular Geometry” Synlett, 7, 922-936 (2003).

  10. T. M. Krygowski, M. K. Cyrański, „Two Faces of the Structural Aspects of Aromaticity” Physical Chemistry Chemical Physics,6, 249-255 (2004).

  11. M. K. Cyranski, "Energetic Aspects of Cyclic Pi-Electron Delocalization - Evaluation of the Methods of Estimating Aromatic Stabilization Energies" Chem. Rev., 105, 3773-3811 (2005)

  12. A. Adamczyk-Wozniak, M. K. Cyranski, A. Zubrowska, A. Sporzynski, "Benzoxaboroles - Old compounds with new applications", Journal of Organometallic Chemistry, 694, 3533-3541 (2009)

Monographs

  1. T. M. Krygowski, M. K. Cyranski, Preface, Aromaticity in Heterocyclic Compounds (T. M. Krygowski, M. K. Cyranski Edts), Vol 19 Topics in Heterocyclic Chemistry (R. R. Gupta Ed), vii-xii, Springer-Verlag, Berlin, Heidelberg (2009)

Last Updated on Tuesday, 13 December 2016 08:01  


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