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Dismantling the Hyperconjugation of π‐Conjugated Phosphorus Heterocycles
Author(s) -
Larrañaga Olatz,
RomeroNieto Carlos,
de Cózar Abel
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201900225
Subject(s) - hyperconjugation , phosphorus , conjugated system , natural bond orbital , computational chemistry , chemistry , organic chemistry , density functional theory , molecule , polymer
The development of π‐extended phosphorus heterocycles has been rapidly increasing because of their unique optoelectronics properties, which are very often considered to be a consequence of special hyperconjugative interactions. However, the latter interactions have primarily been investigated within the five‐membered species, phospholes, and they are often conceptually extrapolated to the rest of π‐extended phosphorus heterocycles (including six‐membered P‐heterocycles) despite evident structural differences. Herein, we report, for the first time, a detailed investigation that sheds light on the hyperconjugative effects of a series of phosphorus heterocyclic systems by means of EDA and NBO calculations within a DFT framework. Our results lay the foundations for the future design of π‐extended phosphorus heterocycles with improved optoelectronics properties.