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Number of results

Journal

2011 | 9 | 1 | 94-105

Article title

The intermolecular interactions in the aminonitromethylbenzenes

Content

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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. [...]

Publisher

Journal

Year

Volume

9

Issue

1

Pages

94-105

Physical description

Dates

published
1 - 2 - 2011
online
16 - 12 - 2010

Contributors

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

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Document Type

Publication order reference

Identifiers

YADDA identifier

bwmeta1.element.-psjd-doi-10_2478_s11532-010-0118-8
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