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Probing a General Rule towards Thermodynamic Stabilities of Mono BN‐doped Lower Polyenes
Author(s) -
Rouf Alvi Muhammad,
Wu Jingjing,
Zhu Jun
Publication year - 2017
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201601753
Subject(s) - heteroatom , methylene , chemical stability , chemistry , boron , doping , computational chemistry , conjugated system , boranes , adsorption , stereochemistry , organic chemistry , materials science , ring (chemistry) , polymer , optoelectronics
The BN‐doped organic analogues are interesting as aliphatic amineboranes for hydrogen storage, precursors for aromatic borazines and adsorbent cage azaboranes. However, BN‐doped aliphatic polyenes remained undeveloped. Herein, we perform theoretical calculations on two mono BN‐doped aliphatic lower polyenes, 1,3‐butadiene and 1,3,5‐hexatriene. A general rule is proposed, i.e., isomers with terminal nitrogen and directly BN‐connected, N−B(R), in particular, are of significant thermodynamic stability as compared with their inverse analogues (where boron is at the terminal position). The N−B(R) type isomers are found to be the most stable ones in both polyenes. Isomers with terminal B and N are of intermediate stability. Highly destabilized isomers are those with one terminal methylene group and one terminal heteroatom in the butadiene series, and two terminal methylene groups in the hexatriene series. Rules established here may lead researchers to synthesize isomers with particular thermodynamic stability.