NDLI: Can the substituent in the para position of anilide ion influence the N$^{−}$···H–F → N–H···F$^{−}$ switching: a quantum chemical study

Content Provider	Springer Nature Link
Author	Roohi, Hossein Roshan, Keumars khastean, Roghayeh
Copyright Year	2012
Abstract	The effect of substituents in the para position of anilide ion (An) on the N$^{−}$···H–F → N–H···F$^{−}$ switching in X–An–HF (X = H, Me, CHO, CN, NO, F, NO$_{2}$, OH and OMe) complexes was investigated by means of B3LYP and MP2 quantum chemical methods. To delve into the mechanistic details of the proton transfer process, potential energy curve and further geometrical parameters involved in H-bonding during the course of the proton transfer process were evaluated at the MP2/6-311++G(2d,2p) level of theory. The changes in H-bond strength because of variation of substituents were well accompanied by changes in formation energy of complexes, structural parameter, electron density, natural charge and charge transfer between subunits. For X = H, Me, CHO, CN, NO, F and NO$_{2}$ substituents, our results at MP2/6-311++G(2d,2p) level showed that the minimum energy structures correspond to the N···HF H-bonded complexes without proton transfer occurring. On the other hand, for electron-donating substituents OH and OMe, proton is transferred from HF to anilide ion and the minimum energy structures are HNH···F$^{−}$ H-bonded complexes. The nature of HN$^{−}$···HF and HN–H···F$^{−}$ interactions in complexes was characterized by means of atoms in molecules and natural bond orbital analyses.
Starting Page	1319
Ending Page	1330
Page Count	12
File Format	PDF
ISSN	10400400
Journal	Structural Chemistry
Volume Number	24
Issue Number	4
e-ISSN	15729001
Language	English
Publisher	Springer US
Publisher Date	2012-11-29
Publisher Place	Boston
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Proton transfer Anilide ion Substituent effect PEC Formation energy MP2 and DFT methods Computer Applications in Chemistry Physical Chemistry Theoretical and Computational Chemistry
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry Condensed Matter Physics

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