NDLI: Can the positive aromatic ring be as π-electron donor in π-halogen bond? A MP2 theoretical investigation on the unusual π-halogen bond interaction between three-membered ring $$ \left( {\hbox{BNN}} \right)

Content Provider	Springer Nature Link
Author	Qi, Hai tao Ren, Fu de Zhang, Jing lin Wang, Jing yu
Copyright Year	2010
Abstract	The unusual π-halogen bond interactions are investigated between $$ \left( {\hbox{BNN}} \right)_3^{+} $$ and X1X2 (X1, X2 = F, Cl, Br) employing MP2 at 6-311 + G(2d) and aug-cc-pVDZ levels according to the “CP (counterpoise) corrected potential energy surface (PES)” method. The order of the π-halogen bond interactions and stabilities of the complexes are obtained to be $$ \left( {\hbox{BNN}} \right)_3^{+} \ldots {{\hbox{F}}_2} < \left( {\hbox{BNN}} \right)_3^{+} \ldots {\hbox{ClF < }}\left( {\hbox{BNN}} \right)_3^{+} \ldots {\hbox{C}}{{\hbox{l}}_2} < \left( {\hbox{BNN}} \right)_3^{+} \ldots {\hbox{BrCl}}\quad { < }\quad \left( {\hbox{BNN}} \right)_3^{+} \ldots {\hbox{B}}{{\hbox{r}}_2}\quad { < }\quad \left( {\hbox{BNN}} \right)_3^{+} \ldots {\hbox{BrF}}{.} $$ at MP2/aug-cc-pVDZ level. The analyses of the Mulliken charge transfer, natural bond orbital (NBO), atoms in molecules (AIM) theory and electron density shifts reveal that the nature of the π-halogen bond interaction in the complexes of ClF, BrF and BrCl might partly be charge transfer from the delocalized π-HOMO orbital of $$ \left( {\hbox{BNN}} \right)_3^{+} $$ to X1X2. This result suggests that the positive aromatic ring $$ \left( {\hbox{BNN}} \right)_3^{+} $$ might act as a π-electron donor to form the π-halogen bond. Figure Shifts of electron density as a result of formation of the complex. The unusual π-halogen interactions are found between (BNN)3 + and X1X2 (X1, X2=F, Cl, Br) employing MP2 method at 6-311+G(2d) and aug-cc-pVDZ levels according to the “CP-corrected PES)” method. The analyses of the Mulliken charge transfer, NBO, AIM and electron density shifts reveal that the nature of the π-halogen bond interaction in the complexes of ClF, BrF and BrCl might partly be charge transfer from the delocalized π-HOMO orbital of (BNN)3 + to X1X2. (BNN)3 + might be as π-electron donor to form the π-halogen bond.
Starting Page	929
Ending Page	937
Page Count	9
File Format	PDF
ISSN	16102940
Journal	Journal of Molecular Modeling
Volume Number	17
Issue Number	5
e-ISSN	09485023
Language	English
Publisher	Springer-Verlag
Publisher Date	2010-07-06
Publisher Place	Berlin, Heidelberg
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	$$ \left( {\hbox{BNN}} \right)_3^{+} $$ Electron density shifts MP2 π-electron donor π-halogen bond interaction Computer Applications in Chemistry Life Sciences Biomedicine general Health Informatics Molecular Medicine Computer Application in Life Sciences
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Physical and Theoretical Chemistry Computational Theory and Mathematics Catalysis Inorganic Chemistry Computer Science Applications

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