Aromatic Character of the Benzene Ring Present in Various Topological Environments in Benzenoid Hydrocarbons. Nonequivalence of Indices of Aromaticity

Journal of Chemical Information and Computer Sciences

Volumn 35, Issue 2, 1995, Pages 203-210

  Krygowski, Tadeusz Marek ^a   Ciesielski, Arkadiusz ^a   Bird, Clive William ^b   Kotschy, Andras ^b  

^a UNIVERSITY OF WARSAW   (Poland)

^b KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBONS; CHEMICAL BONDS; CORRELATION METHODS; ELECTRON DIFFRACTION; ESTIMATION; GEOMETRY; INTERPOLATION; MOLECULAR STRUCTURE; NEUTRON DIFFRACTION; REGRESSION ANALYSIS; X RAY DIFFRACTION;

AROMATICITY INDICES; BENZENOID HYDROCARBONS; BOND ENERGY; FACTOR ANALYSIS; HEAT OF FORMATION; HETEROGENEOUS MOLECULAR SYSTEMS; TOPOLOGICAL ENVIRONMENTS;

BENZENE;

EID: 0029271229     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci00024a006     Document Type: Article

References (60)

1. Kekulé, A. Über die Constitution der aromatischen Substanzen. Bull. Soc. Chim. Fr. 1865, 3, 98.
2. Erlenmayer, E. Studien Über die sogenanten aromatischen Saiiren. Am. Chem. Pharm. 1866, 137, 327.
3. Sondheimer, F. The Chemistry of Annulenes. Pure Appl. Chem. 1964, 7, 363.
4. Aromaticity, Pseudoaromaticity and Anti-aromaticity; Bergmann, E. D., Pullman, B., Eds.; Israel Academy of Sciences and Humanities: Jerusalem, 1971.
5. Shaik S. S.; Hiberty, P. C.; Lefour, J. M.; Ohanessian, G. Is Delocalization a Driving Force in Chemistry? J. Am. Chem. Soc. 1987, 109, 363.
6. Jug, K.; Koster, A. M. Influence of a and Electrons on Aromaticity. J. Am. Chem. Soc. 1990, 112, 6772.
7. Malinowski, E. R.; Howery, D. G. Factor Analysis in Chemistry; Wiley Interscience: 1980; New York.
8. Katritzky, A. R.; Barczyñski, P.; Musumarra, G.; Pisano, D.; Szafran, M. Aromaticity as a Quantitative Concept. 1. A Statistical Demonstration of the Orthogonality of “Classical” and “Magnetic” Aromaticity in Five-and Six-Membered Heterocycles. J. Am. Chem. Soc. 1989, 111, 7.
9. Katritzky, A. R.; Feygelman, V.; Musumarra, G.; Barczyñski, P.; Szafran, M. Aromaticity as a Quantitative Concept. 2. Sixteen Familiar Five-and Six-membered Monocyclic Heterocycles. J. Prakt. Chem. 1990, 332, 853.
10. Katritzky, A. R.; Feygelman, V.; Musumarra, G.; Barczyñski, P.; Szafran, M. Aromaticity as a Quantitative Concept. 3. Benzo-fused Five-and Six-membered Heterocycles. J. Prakt. Chem. 1990, 332, 870.
11. Katritzky, A. R.; Barczyñski, P. Aromaticity as a Quantitative Concept. 4. Less Familiar Five-and Six-membered Monocyclic Heterocycles. J. Prakt. Chem. 1990, 332, 885.
12. Jug, K.; Koster, A. M. Aromaticity as a Multi-Dimensional Fenomenon. J. Phys. Org. Chem. 1991, 4, 163.
13. Bird, C. W. A. New Aromaticity Index and its Application to Fivemembered Ring Heterocycles. Tetrahedron 1985, 41, 1409.
14. Kruszewski, J.; Krygowski, T. M. Definition of Aromaticity Basing on the Harmonic Oscillator Model. Tetrahedron Lett. 1972, 3842.
15. Krygowski, T. M. Crystallographic Studies of Inter-and Intramolecular Interactions Reflected in Aromatic Character of-Electron Systems. J. Chem. Inf. Comput. Sci. 1993, 33, 70.
16. Jug, K. A. Bond Order Approach to Ring Current and Aromaticity. J. Org. Chem. 1983, 48, 1344.
17. Binsch, G.; Heilbronner, E. Double Bond Fixation in Non-Altemant-Electron Systems. Tetrahedron 1968, 24, 1215.
18. Pozharski, A. F. Chem. Heterocycl. Comp. 1985, 21, 717.
19. Krygowski, T. M.; Kalinowski, M. K.; Turowska-Tyrk, I.; Hiberty, P. C.; Milart, P.; Silvestre, A.; Topsom, R. D.; Daehne, S. Crystallographic Studies of Inter-and Intramolecular Interactions. Part 4. A Comparative Study of the Effect of Through-Resonance on the Geometry of p-Nitro-and p-Nitrosophenolate Anions. Struct. Chem. 1991, 2, 71.
20. Pauling, L. Atomic Radii and Interatomic Distances in Metals. J. Am. Chem. Soc. 1947, 69, 542.
21. Bürgi, H.-B. Stereochemistry of Reaction Paths as Determined from Crystal Structure Data–A Relationship between Structure and Energy. Angew. Chem., Int. Ed. Engl. 1975, 14, 460.
22. Johnston, H. S.; Parr, C. H. Activation Energies from Bond Energies. I. Hydrogen Transfer Reactions. J. Am. Chem. Soc. 1963, 84, 2544.
23. Longuett-Higgins, H. C.; Salem, L. The Alternation of Bond Lengths in Long Conjugated Chain Molecules. Proc. Roy. Soc. 1959, 251A, 172.
24. Hedberg, K.; Schomaker, V. The Reinvestigation of the Structures of Diborane and Ethane by Electron Diffraction. J. Am. Chem. Soc. 1951, 73, 1482.
25. Bartell, L. S.; Roth, E. A.; Hollowell, C. D.; Kuchitsu, K.; Young, J. E., Jr. Electron-Diffraction Study of the Structures of C2H4 and C2D4. J. Chem. Phys. 1965, 42, 2683.
26. George, P. A. Critique of the Resonance Energy Concept with Particular Reference to Nitrogen Heterocycles, Especially Porphyrins. Chem. Rev. 1975, 75, 85.
27. Stoicheff, B. P. Can. J. Phys. 1954, 32, 334.
28. Jeffrey, G. A.; Ruble, J. R.; McMullan, R. K.; Pople, J. A. The Crystal Structure of Deuterated Benzene. Proc. Roy. Soc. Ser. A 1987, 414, 47.
29. Cox, J. D.; Croickshank, D. W. L.; Smith, J. A. S. Crystal Structure of Benzene: A New Type of Systematic Error in Precision X-ray Crystal Analysis. Nature 1955, 175, 766.
30. Furka, A.; Sebastyn, F. Do the C-H Bonds Contribute to the Stabilisation Energy of Benzene? Croat. Chem. Acta 1980, 53, 555.
31. Hafelinger, G. Similarity Models in Organic Chemistry, Biochemistry and Related Fields; Zalewski, R. I., Krygowski, T. M., Shorter, J., Eds.; Elsevier: Amsterdam, 1991; Chapter 4.
32. Allen, F. H.; Bellard, S.; Brice, M. D.; Cartwright, B. A.; Doubleday, A.; Higgs, H.; Hummelink, T. W. A.; Hummelink-Peters, B. G. M. C.; Kennard, O.; Motherwell, W. D. S.; Rodgers, J. R.; Watson, D. G. The Cambridge Crystallographic Data Centre: Computer-Based Search, Retrieval, Analysis and Display of Information. Acta Crystallogr. Sect. B 1979, 35, 2331.
33. Allen, F. H.; Davies, J. E.; Galloy, J. J.; Johnson, O.; Kennard, O.; McRae, Mitchell, E. M.; Mitchell, G. F.; Smith, J. M.; Watson, D. G. The Development of Versions 3 and 4 of the Cambridge Structural Database System. J. Chem. Inf. Comp. Sci. 1991, 31, 187.
34. Donald, F.; Morrison, Multivariate Statistical Methods’, McGraw-Hill Book Company: English edition copyright 1967; 1976.
35. Randić, M. Chem. Phys. Lett. 1976, 38, 68.
36. Gutman, I.; Cyvin, S. J. Introduction to the Theory of Benzenoid Hydrocarbons’, Springer-Verlag: Berlin, 1989.
37. Ponomarev, V. I.; Filipenko, O. S.; Atovmyan, L. O. KristaUitcheskaya i Molekulamaja Struktura Naftalina pri-150 °C (in Russian). Kristallogr. 1976, 21, 392.
38. Brock, C. P.; Dunitz, J. D. Temperature Dependence of Thermal Motion in Crystalline Naphthalene. Acta Crystallogr. B1982,38,2218.
39. Kay, M. I.; Okaya, Y.; Cox, D. E. A. Refinement of the Structure of the Room Temperature Phase of Phenanthrene, C14H10, from X-ray and Neutron Diffracrtion Data. Acta Crystallogr. B 1971, 27, 26.
40. Hirshfeld, F. L.; Sandler, S.; Schmidt, G. M. J. The Structure of Overcrowded Aromatic Compounds. Part VI. The Crystal Structure of Benzo[c]phenenthrene and of 1,12-Dimethylbenzojcjphenanthrene J. Chem. Soc. 1963, 2108.
41. Mason, R. The Crystallography of Anthracene at 95K and 290K. Acta Crystallogr. 1964, 17, 547.
42. Ponomarev, V. I.; Shilov, G. V. KristaUitcheskaya struktura antracena v intervale 300-100 K (in Russian). Kristallograf. 1983, 28, 674.
43. Robertson, J. M.; White, J. G. The Crystal Structure of the Monoclinic Modification of 1:2-5:6-Dibenzanthracene. A Quantitative X-ray Investigation. J. Chem. Soc. 1956, 925.
44. Herbstein, F. H. Crystal and Molecular Structures of Overcrowded Halogenated Compounds. VIII. Two Overcrowded Naphthalenes– Octachloronaphtalene and Tetrabenzonaphthalene (Dibenzo[g,p]chrysene). Acta Crystallogr. B 1979, 35, 1661.
45. Ferraris, G.; Jones, D. W.; Yerkess, J. A. Neutron-Diffraction Study of the Crystal and Molecular Structure of Triphenylene. Z Kristallogr. 1973, 138, 113.
46. Kai, Y.; Hama, F.; Yasuoka, M.; Kasai, N. Structural Chemistry of Layered Cyclophanes. III. Molecular Structures of [2.2](2,7)-Pyrenophane-1,1 ‘-diene and Pyrene (Redeterminated). Acta Crystallogr. B 1978, 34, 1263.
47. De, A.; Gosh, R.; Roychowdhury, S.; Roychowdhury, P. Structural Analysis of Picene, C22H14. Acta Crystallogr. C 1985, 41, 907.
48. Marsh, W.; Dunitz, J. D. Crystal Structure of a Double Helicene, Diphenanthro[3,4-a; 3’,4'-o]picene. Bull. Soc. Chim. Belg. 1979, 88, 847.
49. Krygowski, T. M.; Ciesielski, A.; Swirska, B.; Leszczynski, P. Variation of Molecular Geometry and Aromatic Character of Chrysene and Perylene in Their EDA complexes. Refinement of X-ray Crystal and Molecular Structure of Chrysene and Perylene. Pol. J. Chem. 1994, 68, 2097.
50. Kohno, Y.; Kohno, M.; Sai to, Y.; Inokuchi, H. The Crystal Structure of Tetrabenzo[u,cdy,im]perylene. Acta Crystallogr. B 1975,31, 2076.
51. Kuroda, R. J. Crystal and Molecular Structure of [SjHelicene: Crystal Packing Models. J. Chem. Soc., Perkin Trans 2 1982, 789.
52. de Rango, C.; Tsoucaris, G.; Declercq, J. P.; Germain, G.; Putzeys, J. P. Hexahelicene. Crystallogr. Struct. Commun. 1973, 2, 189.
53. Beurskens, P. T.; Beurskens, G.; van der Hark, T. E. M. Heptahelicene. Crystallogr. Struct. Commun. 1976, 5, 241.
54. Oonishi, I.; Ohshima, S.; Fujisawa, S.; Aoki, J.; Ohashi, Y.; Krygowski, T. M. Conformation of Condensed Polycyclic Aromatic Hydrocarbons. The Crystal and Molecular Structure of Tribenzo[a,/t,rrf]phenanthrajl, 2,10-cdejpentaphene. J. Mol. Struct. 1992, 265, 283.
55. Fujisawa, S.; Oonishi, I.; Aoki, J.; Ohashi, Y. Structure of Dibenzo-[dc/,i]naphto[l,8,7-vwx]pyranthrene. Acta Crystallogr. 1986, C42, 1390.
56. Fujisawa, S.; Oonishi, I.; Aoki, J.; Ohashi, Y.; Sasada, Y. Conformation of Condensed Polycyclic Aromatic Hydrocarbons. I. The Molecular and Crystal Structure of Anthra[2,1,9,8-/u/k/]benzo[de]naphtho[2,1,8,7-riuvjpentacene. Bull. Chem. Soc. Jpn. 1982, 55, 3424.
57. Kerr, K. A.; Ashmore, J. P.; Speakman, J. C. The Crystal and Molecular Structure of Quaterrylene: A Redetermination. Proc. Roy. Soc. London Ser. A 1975, 344, 199.
58. Hazell, R. G.; Pawley, G. S. The Crystal and Molecular Structure of Ovalene: Some Three-Dimentional Refinements. Z. Kristallogr. 1973, 137, 159.
59. Izuoka, A.; Wakui, K.; Fukuda, T.; Sato, N.; Sugawara, T. Refined Molecular Structure of Tetrabenzo[de,Ai,op,rt]pentacene. Acta Crystallogr. C 1992, 48, 900.
60. Pedley, J. B.; Naylor, R. D.; Kirby, S. P. Thermochemical Data of Organic Compounds’, Chapman and Hall: London, 1986.