Out of cross-conjugation: The unexpected structure of tetrazinones

A. Bényei, A. Stirling, B. Bostai, K. Lrincz, A. Kotschy

Research output: Contribution to journalArticle

Abstract

Detailed structural and computational investigations have been carried out to elucidate the unprecedented structural properties of NHC-derived tetrazinones. The provocative structural contradictions featured by this class of molecules as emerged from single crystal X-ray diffraction studies include the non-coplanar core ring system with an inter-ring C-C single bond indicating aromaticity but a pattern of bond alteration consistent with an overall quinoidal structure. Combination of periodic and gas-phase calculations identified two key factors affecting the overall structure. The first is a strong tendency to avoid cross-conjugation resulting in a coupled aromatic-quinoidal system whereas the second is the steric demand of the substituents determining the conformational behaviour of the rings. The peculiar electron distribution yields remarkably large polarizations and dipole moments for these molecules which can be key in their potential applications. This journal is

Original languageEnglish
Pages (from-to)47762-47768
Number of pages7
JournalRSC Advances
Volume4
Issue number88
DOIs
Publication statusPublished - 2014

Fingerprint

Molecules
Dipole moment
Structural properties
Gases
Single crystals
Polarization
X ray diffraction
Electrons
single bond

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Chemistry(all)

Cite this

Out of cross-conjugation : The unexpected structure of tetrazinones. / Bényei, A.; Stirling, A.; Bostai, B.; Lrincz, K.; Kotschy, A.

In: RSC Advances, Vol. 4, No. 88, 2014, p. 47762-47768.

Research output: Contribution to journalArticle

Bényei, A. ; Stirling, A. ; Bostai, B. ; Lrincz, K. ; Kotschy, A. / Out of cross-conjugation : The unexpected structure of tetrazinones. In: RSC Advances. 2014 ; Vol. 4, No. 88. pp. 47762-47768.
@article{0bd5a9f9eacb4fe8a985403f8ec033dd,
title = "Out of cross-conjugation: The unexpected structure of tetrazinones",
abstract = "Detailed structural and computational investigations have been carried out to elucidate the unprecedented structural properties of NHC-derived tetrazinones. The provocative structural contradictions featured by this class of molecules as emerged from single crystal X-ray diffraction studies include the non-coplanar core ring system with an inter-ring C-C single bond indicating aromaticity but a pattern of bond alteration consistent with an overall quinoidal structure. Combination of periodic and gas-phase calculations identified two key factors affecting the overall structure. The first is a strong tendency to avoid cross-conjugation resulting in a coupled aromatic-quinoidal system whereas the second is the steric demand of the substituents determining the conformational behaviour of the rings. The peculiar electron distribution yields remarkably large polarizations and dipole moments for these molecules which can be key in their potential applications. This journal is",
author = "A. B{\'e}nyei and A. Stirling and B. Bostai and K. Lrincz and A. Kotschy",
year = "2014",
doi = "10.1039/c4ra05616g",
language = "English",
volume = "4",
pages = "47762--47768",
journal = "RSC Advances",
issn = "2046-2069",
publisher = "Royal Society of Chemistry",
number = "88",

}

TY - JOUR

T1 - Out of cross-conjugation

T2 - The unexpected structure of tetrazinones

AU - Bényei, A.

AU - Stirling, A.

AU - Bostai, B.

AU - Lrincz, K.

AU - Kotschy, A.

PY - 2014

Y1 - 2014

N2 - Detailed structural and computational investigations have been carried out to elucidate the unprecedented structural properties of NHC-derived tetrazinones. The provocative structural contradictions featured by this class of molecules as emerged from single crystal X-ray diffraction studies include the non-coplanar core ring system with an inter-ring C-C single bond indicating aromaticity but a pattern of bond alteration consistent with an overall quinoidal structure. Combination of periodic and gas-phase calculations identified two key factors affecting the overall structure. The first is a strong tendency to avoid cross-conjugation resulting in a coupled aromatic-quinoidal system whereas the second is the steric demand of the substituents determining the conformational behaviour of the rings. The peculiar electron distribution yields remarkably large polarizations and dipole moments for these molecules which can be key in their potential applications. This journal is

AB - Detailed structural and computational investigations have been carried out to elucidate the unprecedented structural properties of NHC-derived tetrazinones. The provocative structural contradictions featured by this class of molecules as emerged from single crystal X-ray diffraction studies include the non-coplanar core ring system with an inter-ring C-C single bond indicating aromaticity but a pattern of bond alteration consistent with an overall quinoidal structure. Combination of periodic and gas-phase calculations identified two key factors affecting the overall structure. The first is a strong tendency to avoid cross-conjugation resulting in a coupled aromatic-quinoidal system whereas the second is the steric demand of the substituents determining the conformational behaviour of the rings. The peculiar electron distribution yields remarkably large polarizations and dipole moments for these molecules which can be key in their potential applications. This journal is

UR - http://www.scopus.com/inward/record.url?scp=84907889917&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84907889917&partnerID=8YFLogxK

U2 - 10.1039/c4ra05616g

DO - 10.1039/c4ra05616g

M3 - Article

AN - SCOPUS:84907889917

VL - 4

SP - 47762

EP - 47768

JO - RSC Advances

JF - RSC Advances

SN - 2046-2069

IS - 88

ER -