Abstract
Despite significant progress in conformational analysis of cyclic molecules, the number of computational studies is still limited while most of that available in the literature data have been obtained long time ago with outdated methods. In present research, we have studied temperature driven conformational changes of the furan ring at three different temperatures. Additionally, the effect of deuteration on the ring dynamics is discussed; in addition, the aromaticity indices following the Bird and HOMA schemes are computed along all trajectories. Our ab initio molecular dynamic simulations revealed that deuteration has changed the furan ring dynamics and the obvious consequences; in addition, the shape and size of molecule are expected to be different.
Highlights
Isotope effect and aromaticity are the key concepts in modern organic chemistry [1,2,3,4,5] with H/D isotope substitution being one of the fundamental aspects of NMR labeling, Neutron Scattering, and Mass Spectroscopy [6,7,8,9,10].Furan is a cyclic aromatic ether found in cigarette smoke and used in the production of resins [11] and some agrochemicals and pharmaceuticals
It is said that the presence of an aromatic conjugated system is responsible for bond equalization and most importantly the planarity of the ring. These statements seem to be in agreement with many experimental and theoretical studies [17,18,19] for many decades, rings with aromatic character have been considered as flat and conformationally rigid molecules, until the recent theoretical studies [20,21,22,23] based on ab initio calculations, both at T = 0 K and with T > 0 K, that have shown the large amount of flexibility of aromatic molecules
We investigated furan ring dynamics at three different temperatures taking into account the effect of deuteration on ring puckering
Summary
Isotope effect and aromaticity are the key concepts in modern organic chemistry [1,2,3,4,5] with H/D isotope substitution being one of the fundamental aspects of NMR labeling, Neutron Scattering, and Mass Spectroscopy [6,7,8,9,10].Furan is a cyclic aromatic ether found in cigarette smoke and used in the production of resins [11] and some agrochemicals and pharmaceuticals. It is said that the presence of an aromatic conjugated system is responsible for bond equalization and most importantly the planarity of the ring. These statements seem to be in agreement with many experimental and theoretical studies [17,18,19] for many decades, rings with aromatic character have been considered as flat and conformationally rigid molecules, until the recent theoretical studies [20,21,22,23] based on ab initio calculations, both at T = 0 K and with T > 0 K, that have shown the large amount of flexibility of aromatic molecules
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