The intermolecular interactions in the aminonitromethylbenzenes |
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Authors: | Rafal Kruszynski Tomasz Sieranski |
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Institution: | 1.Department of X-Ray Crystallography and Crystal Chemistry, Institute of General and Ecological Chemistry,Technical University of Lodz,?ód?,Poland |
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Abstract: | 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.
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