Varying electronegativity: Effect of the nature and strength of H-bonding in anilide/aniline/anilinium complexes on the electronegativity of NH- / NH2 / NH3+ groups

Journal of Molecular Structure

Volumn 844-845, Issue , 2007, Pages 200-207

  Szatyłowicz, Halina ^a   Krygowski, Tadeusz M ^b  

^a WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

^b UNIVERSITY OF WARSAW   (Poland)

Author keywords

Anilide anion; Aniline; Anilinium cation; Electronegativity; Group electronegativity; Hydrogen bond

Indexed keywords

COMPLEXATION; DERIVATIVES; ELECTRONEGATIVITY; HYDROGEN BONDS; MOLECULAR MODELING; SUBSTITUTION REACTIONS;

ANGULAR GEOMETRY; ANILIDE ANIONS; ANILINIUM CATIONS; GROUP ELECTRONEGATIVITY;

ANILINE;

EID: 35348864999     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2007.04.018     Document Type: Article

References (70)

1. Campanelli A.R., Domenicano A., Ramondo F., and Hargittai I. J. Phys. Chem. A 108 (2004) 4940
2. Allen F.H. Acta Crystallogr. Sec. B: Struct. Sci. 58 (2002) 380
3. McWeeney R. Coulson's Valence. third ed. (1979), Oxford University Press, Oxford Introduction
4. Pauling L. The Nature of the Chemical Bond (1960), Cornell Univ. Press, Ithaca pp. 88
5. Mulliken R.S. J. Chem. Phys. 2 (1934) 782
6. Allred A.L., and Rochow E.G. J. Inorg. Nucl. Chem. 5 (1958) 264
7. Gordy W. Phys. Rev. 69 (1946) 604
8. Walsh A.D. Proc. Roy. Soc. (Lond.) A207 (1951) 13
9. Gordy W. J. Chem. Phys. 19 (1951) 792
10. Sanderson R.T. J. Chem. Phys. 23 (1955) 2467
11. Pritchard H.O., and Skinner H.A. Chem. Rev. 55 (1955) 745
12. Boyd R.J., and Markus G.E. J. Chem. Phys. 75 (1981) 5385
13. Iczkowski R.P., and Margrave J.L. J. Am. Chem. Soc. 83 (1961) 3547
14. Huheey J.E. J. Phys. Chem. 69 (1965) 3284
15. Huheey J.E. J. Phys. Chem. 70 (1966) 2086
16. Imamoto N., and Masuda S. Tetrahedron Lett. (1977) 3287
17. Hinze J., and Jaffe H.H. J. Am. Chem. Soc. 84 (1962) 540
18. Marriot S., Reynolds W.F., Taft R.W., and Topsom R.D. J. Org. Chem. 49 (1984) 959
19. Suresh C.H., and Koga N. J. Am. Chem. Soc. 124 (2002) 1790
20. Politzer P., Murray J.S., and Grice M.E. Coll. Czech. Chem. Commun. 70 (2005) 550
21. Pauling L. J. Am. Chem. Soc 54 (1932) 3570
22. Walsh A.D. Discuss. Farad. Soc. 2 (1947) 18
23. Sanderson R.T. J. Chem. Educ. 31 (1954) 2
24. Mullay J. J. Am. Chem. Soc. 107 (1985) 7271
25. Boyd R.J., and Boyd S.L. J. Am. Chem. Soc. 114 (1992) 1652
26. Reed L.H., and Allen L.C. J. Phys. Chem. 96 (1992) 157
27. De Proft F., Langenacker W., and Geerlings P. J. Phys. Chem. 97 (1993) 1826
28. Suresh C.H., and Koga N. J. Am. Chem. Soc. 124 (2002) 1790
29. Domenicano A., Vaciago A., and Coulson C. Acta Crystallogr. B31 (1975) 1630
30. Domenicano A., Mazzeo P., and Vaciago A. Tetrahedron Lett. 17 (1976) 1029
31. Malinowski E.R. Factor Analysis in Chemistry. third ed. (2002), Wiley-Interscience, New York pp. 255-294
32. Zalewski R.I. In: Zalewski R.I., Krygowski T.M., and Shorter J. (Eds). Similarity Models in Organic Chemistry, Biochemistry and Related Fields, Studies in Organic Chemistry vol. 42 (1991), Elsevier, Amsterdam Chapter 9
33. Campanelli A.R., Domenicano A., and Ramondo F. J. Phys. Chem. A 107 (2003) 6429
34. Domenicano A., Murray-Rust P., and Vaciago A. Acta Crystallogr. B39 (1983) 457
35. Krygowski T.M., and Szatyłowicz H. J. Phys. Chem. A 110 (2006) 7232
36. Krygowski T.M., Zachara J.E., and Szatyłowicz H. J. Phys. Org. Chem. 18 (2005) 110
37. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T.; Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03, Revision C.02, Gaussian, Inc., Wallingford, CT, 2004.
38. Boys S.F., and Bernardi F. Mol. Phys. 19 (1970) 553
39. Bondi A. J. Phys. Chem. 68 (1964) 441
40. Szatylowicz H., Krygowski T.M., and Hobza P. J. Phys. Chem. A 111 (2007) 170
41. Abboud K.A., Villanueva L.A., and Boncella J.M. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 49 (1993) 1848
42. Barnett S.A., Johnston A., Florence A.J., and Kennedy A.R. Acta Crystallogr. Sect. E: Struct. Rep. Online 61 (2005) o2318
43. Fukuyo M., Hirotsu K., and Higuchi T. Acta Crystallogr. Sect.B: Struct. Crystallogr. Cryst. Chem. 38 (1982) 640
44. Aitipamula S., and Nangia A. Chem.-Eur. J. 11 (2005) 6727
45. Bourne S.A., Corin K.C., Nassimbeni L.R., and Weber E. Cryst. Eng. Comm. 6 (2004) 54
46. Jacobs A., Nassimbeni L.R., and Taljaard J.H. Cryst. Eng. Comm. 7 (2005) 731
47. Loehlin J.H., Etter M.C., Gendreau C., and Cervasio E. Chem. Mater. 6 (1994) 1218
48. Johnston A., Florence A.J., and Kennedy A.R. Acta Crystallogr. Sect. E: Struct. Rep. Online 61 (2005) o2520
49. Idrissi A.K., Rafiq M., Gougeon P., and Guerin R. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 51 (1995) 1359
50. Dolbecq A., Fourmigue M., Krebs F.C., Batail P., Canadell E., Clerac R., and Coulon C. Chem.-Eur. J. 2 (1996) 1275
51. Paixao J.A., Matos Beja A., Ramos Silva M., Alte da Veiga L., and Martin-Gil J. Z. Kristallogr.-New Cryst. Struct. 214 (1999) 85
52. Tacke R., Burschka C., Richter I., Wagner B., and Willeke R. J. Am. Chem. Soc. 122 (2000) 8480
53. Paixao J.A., Beja A.M., Silva M.R., and Martin-Gil J. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 56 (2000) 1132
54. Montchamp J.-L., and Dumond Y.R. J. Am. Chem. Soc. 123 (2001) 510
55. Angelov C.M., van den Heever J.P., McDonald R., McEwan A.J.B., and Mercer J.R. Acta Crystallogr. Sect. E: Struct. Rep. Online 58 (2002) o498
56. Mahmoudkhani A.H., and Langer V. J. Mol. Struct. 609 (2002) 55
57. Mahmoudkhani A.H., and Langer V. Cryst. Growth Des. 2 (2002) 21
58. Perpetuo G.J., and Janczak J. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 59 (2003) o709
59. Rademeyer M. Acta Crystallogr. Sect. E: Struct. Rep. Online 60 (2004) o958
60. Smith G., Wermuth U.D., and Healy P.C. Acta Crystallogr. Sect. E: Struct. Rep. Online 60 (2004) o1800
61. Marchewka M.K., and Pietraszko A. J. Phys. Chem. Solids 66 (2005) 1039
62. Glidewell C., Low J.N., Skakle J.M.S., and Wardell J.L. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 61 (2005) o276
63. Speakman J.C. Struct. Bonding 12 (1972) 141
64. Emsley J. Chem. Soc. Rev. 9 (1980) 91
65. Steiner T. Angew. Chem. Int. Ed. 41 (2002) 48
66. H. Szatylowicz, T.M. Krygowski, J.E. Zachara-Horeglad, J. Chem. Inf. Model (2007), doi:10.1021/ci600502w. Available online 20 April 2007.
67. Mmereki B.T., and Donaldson D.J. J. Phys. Chem. A 106 (2002) 3185
68. McIver R.T., and Silvers J.H. J. Am. Chem. Soc. 95 (1973) 8462
69. McMahon T.B., and Kebarle P. J. Am. Chem. Soc. 99 (1977) 2222
70. Fujio M., McIver R.T., and Taft R.W. J. Am. Chem. Soc. 103 (1981) 4017