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 language | English |
|---|---|
| Pages (from-to) | 47762-47768 |
| Number of pages | 7 |
| Journal | RSC Advances |
| Volume | 4 |
| Issue number | 88 |
| DOIs | |
| Publication status | Published - 2014 |
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ASJC Scopus subject areas
- Chemical Engineering(all)
- Chemistry(all)
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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 journal › Article
}
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 -