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Generalized Anomeric Effect on N-Alkyl-amino Cation Affinities: A G2(+)<sub>M</sub> Investigation.
MedLine Citation:
PMID:  22452350     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
The gas-phase N-alkyl-amino-cation affinities (NAACA) of archetypal anionic main-group element hydrides across the Periodic Table have been investigated by means of a modified G2(+) scheme. The reactions studied include R2NB --> R2N+ + B- (R = H, Me; B = XHn , n = 03, X = F, Cl, Br, O, S, Se, N, P, As, C, Si, Ge). Our calculations indicate that the reasonable linear correlations between NAACA and proton affinities (PA) only exist within the Period 2 anions, including H3C, H2N, HO, and F, or the anions within Periods 34 in the Periodic Table, which is significantly different from the alkyl cations affinities, where there is a reasonable correlation between the computed alkyl cations affinity and PA values of the set of anionic main-group element hydrides. The interesting differences can be ascribed to the generalized anomeric effect induced by n(N) -->sigma*(X-H) negative hyperconjugation found in R2NXHn, with central atom X belonging to Groups 14-16 (X = O, S, Se, N, P, As, C, Si, Ge).
Authors:
Song Geng; Yi Ren; Ning-Bew Wong; Wai-Kee Li
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-3-28
Journal Detail:
Title:  The journal of physical chemistry. A     Volume:  -     ISSN:  1520-5215     ISO Abbreviation:  -     Publication Date:  2012 Mar 
Date Detail:
Created Date:  2012-3-28     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9890903     Medline TA:  J Phys Chem A     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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