Directionality and site selectivity of N⋯Cl halogen bonding in two azaaromatic chloride crystals

Journal of Molecular Structure

Volumn 975, Issue 1-3, 2010, Pages 274-279

  Zhu, Yi Min ^a   Miao, Ti Fang ^a,b   Yang, Yang Yi ^a   Zhuang, Dong Yue ^a   Zheng, Kang Cheng ^a   Wong, Wing Tak ^c  

^a SUN YAT SEN UNIVERSITY   (China)

^b HUAIBEI NORMAL UNIVERSITY   (China)

^c HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

DFT calculations; Directionality; Halogen bonding; Molecular electrostatic potential; Site selectivity

Indexed keywords

CHLORINE COMPOUNDS; ELECTROSTATICS; HYDROGEN BONDS; MOLECULAR INTERACTIONS; SELF ASSEMBLY;

DFT CALCULATION; DIRECTIONALITY; HALOGEN BONDING; MOLECULAR ELECTROSTATIC POTENTIALS; SITE SELECTIVITY;

DENSITY FUNCTIONAL THEORY;

EID: 77953616824     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2010.04.035     Document Type: Article

References (50)

1. Lehn J.M. Angew. Chem. Int. Ed. Eng. 27 (1988) 89
2. Aakeröy C.B., Schultheiss N., Desper J., and Moore C. CrystEngComm 9 (2007) 421
3. Kubicki M. J. Mol. Struct. 698 (2004) 67
4. Lu W.-J., Zhu Y.-M., and Zhong K.-L. Acta Crystallogr. C62 (2006) m448 (and references therein)
5. Wan C.Q., Chen X.D., and Mak T.C.W. CrystEngComm 10 (2008) 475
6. Biswas C., Drew M.G.B., Escudero D., Frontera A., and Ghosh A. Eur. J. Inorg. Chem. 15 (2009) 2238
7. Rissanen R. CrystEngComm 10 (2008) 1107
8. Hauchecorne D., Szostak R., Herrebout W.A., and van der Veken B.J. ChemPhysChem 10 (2009) 2105
9. Riley K.E., and Hobza P. J. Chem. Theory Comput. 4 (2008) 232
10. Triguero S., Llusar R., Polo V., and Fourmigué M. Cryst. Growth Des. 8 (2008) 2241
11. Fox D., Metrangolo P., Pasini D., Pilati T., Resnati G., and Terraneo G. CrystEngComm 10 (2008) 1132
12. Lucassen A.C.B., Karton A., Leitus G., Shimon L.J.W., Martin J.M.L., and van der Boom M.E. Cryst. Growth Des. 7 (2007) 386
13. Shirman T., Lamere J.-F., Shimon L.J.W., Gupta T., Martin J.M.L., and van der Boom M.E. Cryst. Growth Des. 8 (2008) 3066
14. Gattuso G., Notti A., Pappalardo S., Parisi M.F., Pilati T., Resnati G., and Terraneo G. CrystEngComm 11 (2009) 1204
15. Palusiak M., and Grabowski S.J. Struct. Chem. 19 (2008) 5
16. Berski S., Ciunik Z., Drabent K., Latajka Z., and Panek J. J. Phys. Chem. B 108 (2004) 12327
17. Lu Y.-X., Zou J.-W., Wang Y.-H., Jiang Y.-J., and Yu Q.-S. J. Phys. Chem. A 111 (2007) 10781
18. Amezaga N.J.M., Pamies S.C., Peruchena N.M., and Sosa G.L. J. Phys. Chem. A 114 (2010) 552
19. Lu Y.-X., Zou J.-W., Fan J.-C., Zhao W.-N., Jiang Y.-J., and Yu Q.-S. J. Comput. Chem. 30 (2009) 725
20. Clark T., Hennemann M., Murray J.S., and Politzer P. J. Mol. Model. 13 (2007) 291
21. Politzer P., Murray J.S., and Concha M.C. J. Mol. Model. 13 (2007) 643
22. Cauliez P., Polo V., Roisnel T., Llusar R., and Fourmigué M. CrystEngComm 12 (2010) 558
23. Pigge F.C., Vangala V.R., Kapadia P.P., Swenson D.C., and Rath N.P. Chem. Commun. 39 (2008) 4726
24. Santis A.D., Forni A., Liantonio R., Metrangolo P., Pilati T., and Resnati G. Chem. Eur. J. 9 (2003) 3974
25. Liantonio R., Metrangolo P., Meyer F., Pilati T., Navarrini W., and Resnati G. Chem. Commun. 17 (2006) 1819
26. Metrangolo P., Meyer F., Pilati T., Proserpio D.M., and Resnati G. Chem. Eur. J. 13 (2007) 5765
27. Hanson G.R., Jensen P., McMurtrie J., Rintoul L., and Micallef A.S. Chem. Eur. J. 15 (2009) 4156 (and references therein)
28. Metrangolo P., Meyer F., Pilati T., Resnati G., and Terraneo G. Angew. Chem. Int. Ed. 47 (2008) 2 (and references therein)
29. Zhu Y.-M., Feng P.-P., Yang Y.-Y., and Ng S.W. Acta Crystallogr. E66 (2010) m54
30. Cui Y., Mo H.-J., Chen J.-C., Niu Y.-L., Zhong Y.-R., Zheng K.-C., and Ye B.-H. Inorg. Chem. 46 (2007) 6427
31. Yang Y.-Y., Huang Z.-Q., He F., Chen X.-M., and Ng S.W. Z. Anorg. Allg. Chem. 630 (2004) 286
32. Yang Y.-Y., Szeto L., and Wong W.-T. Appl. Organometal. Chem. 17 (2003) 958
33. Yang Y.-Y., Huang Z.-Q., Szeto L., and Wong W.-T. Appl. Organometal. Chem. 18 (2004) 97
34. Lu W.-J., Zhu Y.-M., and Zhong K.-L. Acta Crystallogr. C63 (2007) m4
35. Zhu Y.-M., Zhong K.-L., and Lu W.-J. Acta Crystallogr. E62 (2006) m2688
36. Báthori N., Bihátsi L., Bombicz P., and Czugler M. CrystEngComm 5 (2003) 42
37. de Hoog P., Gamez P., Driessen W.L., and Reedijk J. Tetrahedron Lett. 43 (2002) 6783
38. Sheldrick G.M. SHELXS-97, Program for Crystal Structure Solution (1997), University of Göttingen, Germany
39. G.M. Sheldrick, Institüt für Anorganische Chemie der Universität, Tammanstrasse 4, D-3400, Göttingen, Germany, 1998.
40. 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, V. Bakken, 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 D.01, Gaussian, Inc., Wallingford, CT, 2005.
41. Boys S.F., and Bernardi F. Mol. Phys. 19 (1970) 553
42. Fridman N., Kapon M., Sheynin Y., and Kaftory M. J. Incl. Phenom. Macro. Chem. 54 (2006) 153
43. Rowland R.S., and Taylor R. J. Phys. Chem. 100 (1996) 7384
44. de Hoog P., Robertazzi A., Mutikainen I., Turpeinen U., Gamez P., and Reedijk J. Eur. J. Inorg. Chem. 18 (2009) 2684
45. Poleshchuk O.K., Branchadell V., Brycki B., Fateev A.V., and Legon A.C. J. Mol. Struct. (Theochem.) 760 (2006) 175
46. Jain A., Ramanathan V., and Sankararamakrishnan R. Protein Sci. 18 (2009) 595
47. Ran J., and Hobza P. J. Chem. Theory Comput. 5 (2009) 1180
48. Li Q., Wang N., and Yu Z. J. Mol. Struct. (Theochem.) 847 (2007) 68
49. Li Q., An X., Luan F., Li W., Gong B., and Cheng J. J. Phys. Chem. A 112 (2008) 3985
50. Gung B.W., and Amicangelo J.C. J. Org. Chem. 71 (2006) 9261