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Moving towards Nitrogen‐Based Lewis Acids: A Theoretical Study
Author(s) -
Ullah Sabnam S.,
Kashyap Chayanika,
Guha Ankur K.
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201801145
Subject(s) - chemistry , heteroatom , lewis acids and bases , electrophile , annulation , nitrogen , electron affinity (data page) , computational chemistry , ion , homo/lumo , hydride , electron density , density functional theory , medicinal chemistry , electron , ring (chemistry) , organic chemistry , molecule , catalysis , hydrogen , physics , quantum mechanics
Density functional calculations predict that reduction of heteroatom in cyclic nitrenium ion increases the Lewis acidity. Calculations also predict that annelation is a very effective way of stabilizing cyclic nitrenium ions and increasing the Lewis acidic character at the nitrenium centre. This is supported by the lowering in the energies of LUMO coupled with the high values of electrophilicity index as well as high hydride affinity. Substituents are also likely to influence their Lewis acidity. Electron withdrawing substituents increases their acidity while electron donating substituents decreases the same.