The intermolecular interactions in the aminonitromethylbenzenes

• Authors: Rafal Kruszynski , Tomasz Sieranski
• Languages of publication: EN

Abstracts

EN

The intermolecular non-covalent interactions in aminonitromethylbenzenes namely 2-methyl-4-nitroaniline, 4-methyl-3-nitroaniline, 2-methyl-6-nitroaniline, 4-amino-2,6-dinitrotoluene, 2-methyl-5-nitroaniline, 4-methyl-2-nitroaniline, 2,3-dimethyl-6-nitroaniline, 4,5-dimethyl-2-nitroaniline and 2-methyl-3,5-dinitroaniline were studied by quantum mechanical calculations at RHF/311++G(3df,2p) and B3LYP/311++G(3df,2p) level of theory. The calculations prove that solely geometrical study of hydrogen bonding can be very misleading because not all short distances (classified as hydrogen bonds on the basis of interaction geometry) are bonding in character. For studied compounds interaction energy ranges from 0.23 kcal mol−1 to 5.59 kcal mol−1. The creation of intermolecular hydrogen bonds leads to charge redistribution in donors and acceptors. The Natural Bonding Orbitals analysis shows that hydrogen bonds are created by transfer of electron density from the lone pair orbitals of the H-bond acceptor to the antibonding molecular orbitals of the H-bond donor and Rydberg orbitals of the hydrogen atom. The stacking interactions are the interactions of delocalized molecular π-orbitals of the one molecule with delocalized antibonding molecular π-orbitals and the antibonding molecular σ-orbital created between the carbon atoms of the second aromatic ring and vice versa. [...]

Keywords

EN

Intermolecular interactions; Ab initio; Hydrogen bonding; NBO

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2011
• Volume: 9
• Issue: 1
• Pages: 94-105

Dates

published

1 - 2 - 2011

online

16 - 12 - 2010

Contributors

author

Rafal Kruszynski

• Department of X-Ray Crystallography and Crystal Chemistry, Institute of General and Ecological Chemistry, Technical University of Lodz, 90-924, Łódź, Poland

author

Tomasz Sieranski

• Department of X-Ray Crystallography and Crystal Chemistry, Institute of General and Ecological Chemistry, Technical University of Lodz, 90-924, Łódź, Poland

References

• [1] B.W. Gung, J.C. Amicangelo, J. Org. Chem. 71, 9261 (2006) http://dx.doi.org/10.1021/jo061235h[Crossref]
• [2] M. Elstner, P. Hobza, T. Frauenheim, S. Suhai, E. Kaxiras, J. Chem. Phys. 114, 5149 (2001) http://dx.doi.org/10.1063/1.1329889[Crossref]
• [3] K.L. Copeland, J.A. Anderson, A.R. Farley, J.R. Cox, G.S. Tschumper, J. Phys. Chem. B. 112, 14291 (2008) http://dx.doi.org/10.1021/jp805528v[Crossref]
• [4] J.L. Sague Doimeadios, Cent. Eur. J. Chem. 6, 505 (2008) http://dx.doi.org/10.2478/s11532-008-0062-z[Crossref]
• [5] L. Xu, L. Zhu, S. Wu, X. Chen, Q. Teng, Cent. Eur. J. Chem. 4, 732 (2006) http://dx.doi.org/10.2478/s11532-006-0038-9[Crossref]
• [6] K. Müller-Dethlefsand, P. Hobza, Chem. Rev. 100, 143 (2000) http://dx.doi.org/10.1021/cr9900331[Crossref]
• [7] R.Y. Li, Z.R. Li, D. Wu, Y. Li, W. Chen, C.C. Sun, J. Org. Chem.. 109, 2608 (2009)
• [8] D. Swiatla-Wojcik, A. Pabis, J. Szala, Cent. Eur. J. Chem. 6, 555 (2008) http://dx.doi.org/10.2478/s11532-008-0059-7[Crossref]
• [9] L.R. Rutledge, L.S. Campbell-Verduyn, S.D. Wetmore, Chem. Phys. Lett. 444, 167 (2007) http://dx.doi.org/10.1016/j.cplett.2007.06.090[Crossref]
• [10] M. Ferbinteanu, A. Zaharia, M. A. Gîrţu, F. Cimpoesu, Cent. Eur. J. Chem. 8, 519 (2010) http://dx.doi.org/10.2478/s11532-010-0019-x[Crossref]
• [11] X. Mei, C. Wolf. J. Org. Chem. 70, 2299 (2005) http://dx.doi.org/10.1021/jo0479361[Crossref]
• [12] G.A. Jeffrey, W. Saenger, Hydrogen Bonding in Biological Structures (Springer-Verlag, Berlin, 1991)
• [13] G.A. Jeffrey, An Introduction to Hydrogen Bonding (Oxford University Press, New York, 1997)
• [14] L. Chęcińska, S.J. Grabowski. J. Org. Chem. 109, 2942 (2005)
• [15] R. Kruszynski, Cent. Eur. J Chem. 6, 542 (2008) http://dx.doi.org/10.2478/s11532-008-0067-7[Crossref]
• [16] P. Metrangolo, H. Neukirch, T. Pilati, G. Resnati, Acc. Chem. Res. 38, 386 (2005) http://dx.doi.org/10.1021/ar0400995[Crossref]
• [17] P. Metrangolo, G. Resnati (Eds.), Structure and Bonding 126. Halogen Bonding. Fundamentals and Applications (Springer-Verlag, Berlin, 2008)
• [18] C.A. Hunter, J.K.M. Sanders, J. Am. Chem. Soc. 112, 5525 (1990) http://dx.doi.org/10.1021/ja00170a016[Crossref]
• [19] S.L. Cockroft, C.A. Hunter, K.R. Lawson, J. Perkins, C.J. Urch, J. Am. Chem. Soc. 127, 8594 (2005) http://dx.doi.org/10.1021/ja050880n[Crossref]
• [20] M. L Waters, Curr. Opin. Chem. Biol. 6, 736 (2002) http://dx.doi.org/10.1016/S1367-5931(02)00359-9[Crossref]
• [21] J.M. Ducr, L. Cavallo, J. Phys. Chem. B. 111, 13124 (2007) http://dx.doi.org/10.1021/jp072317s[Crossref]
• [22] C.F. Guerra, E.J. Baerends, F.M. Bickelhaupt, Cent. Eur. J. Chem. 6, 15 (2008) http://dx.doi.org/10.2478/s11532-007-0068-y[Crossref]
• [23] D. Cannon, C. Glidewell, J.N. Low, A. Quesada, J.L. Wardell, Acta Crystallogr. C 57, 216 (2001) http://dx.doi.org/10.1107/S0108270100017984[Crossref]
• [24] L. Shimoni, J.P. Glusker, C.W. Bock, J. Phys. Chem. 100, 2957 (1996) http://dx.doi.org/10.1021/jp952339r[Crossref]
• [25] J. Bernstein, L. Shimoni, R.E. Davis, N.L. Chang, Angew. Chem, Int. Ed. Engl. 34, 1555 (1995) http://dx.doi.org/10.1002/anie.199515551[Crossref]
• [26] R. W. Munn, C.J. Eckhardt, J. Phys. Chem. A 105, 6938 (2001) http://dx.doi.org/10.1021/jp011038g[Crossref]
• [27] R. Hiremath, J.A. Swift, Mol. Cryst. Liq. Cryst. Sci. Technol., Sect. A 456, 95 (2006) http://dx.doi.org/10.1080/15421400600786371[Crossref]
• [28] Z.L. Jing, Q.Z. Zhang, J. Jia, M. Yu, Acta Crystallogr. E 62, 1155 (2006) http://dx.doi.org/10.1107/S1600536806006179[Crossref]
• [29] D. Graham, A.R. Kennedy, C.J. McHugh, W.E. Smith, W.I.F. David, K. Shankland, N. Shankland, New J. Chem. 28, 161 (2004) http://dx.doi.org/10.1039/b309792g[Crossref]
• [30] J. Ellena, G. Punte, B.E. Rivero, J. Chem. Cryst. 26, 319 (1996) http://dx.doi.org/10.1007/BF01677094[Crossref]
• [31] J. Ellena, G. Punte, B.E. Rivero, Acta Crystallogr. C 52, 2074 (1996) http://dx.doi.org/10.1107/S0108270195016234[Crossref]
• [32] R. Kruszynski, Acta Crystallogr. E 61, 2379 (2005) http://dx.doi.org/10.1107/S1600536805020684[Crossref]
• [33] D. Cannon, C. Glidewell, J.N. Low, A. Quesada, J.L. Wardell, Acta Crystallogr. Sect. C 57, 216 (2001) http://dx.doi.org/10.1107/S0108270100017984[Crossref]
• [34] R. Kruszynski, Acta Crystallogr. C 65, 396 (2009) http://dx.doi.org/10.1107/S0108270109020551[Crossref]
• [35] 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 C.02 (Gaussian Inc., Wallingford CT USA, 2004)
• [36] A. Chaudhari, S. Lee, Chem. Phys. 310, 281 (2005), and references therein http://dx.doi.org/10.1016/j.chemphys.2004.11.005[Crossref]
• [37] G. Zhao, C. Duan, Z. Zhou, Q. Wu, J. Lu, J. Mol. Struct. 756, 143, (2005)
• [38] S.I. Kawahara T. Uchimaru, Phys. Chem. Chem. Phys. 2, 2869 (2000) [Crossref]
• [39] J.P. Foster, F.A. Weinhold, J. Am. Chem. Soc. 102, 7211 (1980) http://dx.doi.org/10.1021/ja00544a007[Crossref]
• [40] A.E. Reed, F.A. Weinhold, J. Chem. Phys. 83, 1736 (1985) http://dx.doi.org/10.1063/1.449360[Crossref]
• [41] A.E. Reed, L.A. Curtis, F.A. Weinhold, Chem. Rev. 88, 899 (1988) http://dx.doi.org/10.1021/cr00088a005[Crossref]
• [42] S.F. Boys, F. Bernardi. Mol. Phys. 19, 553 (1970) http://dx.doi.org/10.1080/00268977000101561[Crossref]
• [43] C. M. Breneman, K. B. Wiberg, J. Comp. Chem. 11, 361 (1990) http://dx.doi.org/10.1002/jcc.540110311[Crossref]

Identifiers

DOI

10.2478/s11532-010-0118-8