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Weak σ‐Hole Triel Bond between C 5 H 5 Tr (Tr=B, Al, Ga) and Haloethyne: Substituent and Cooperativity Effects
Author(s) -
Yang Qingqing,
Zhou Bohua,
Li Qingzhong,
Scheiner Steve
Publication year - 2021
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.202000955
Subject(s) - chemistry , substituent , ring (chemistry) , nucleophile , lone pair , cooperativity , crystallography , halogen , atom (system on chip) , benzene , binding energy , stereochemistry , molecule , catalysis , atomic physics , organic chemistry , biochemistry , alkyl , computer science , embedded system , physics
The replacement of a CH group of benzene by a triel (Tr) atom places a positive region of electrostatic potential near the Tr atom in the plane of the aromatic ring. This σ‐hole can interact with an X lone pair of XCCH (X=F, Cl, Br, and I) to form a triel bond (TrB). The interaction energy between C 5 H 5 Tr and FCCH lies in the range between 2.2 and 4.4 kcal/mol, in the order Tr=B