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X-ray diffraction and VT-NMR studies of (E)-3-(piperidinyl)-1-(2 '-hydroxyphenyl)-prop-2-en-1-one

Title
X-ray diffraction and VT-NMR studies of (E)-3-(piperidinyl)-1-(2 '-hydroxyphenyl)-prop-2-en-1-one
Author(s)
Choi, SeunghyunKim, YunHyePark, Bernie ByeonghoonPark, SuziePark, JonghyunOk, KiwonKoo, JaeHyungJung, Yong WooJeon, Young HoLee, Eun HeeLee, Ken S.Byun, Youngjoo
Issued Date
2014-11-05
Citation
Journal of Molecular Structure, v.1076, pp.600 - 605
Type
Article
Author Keywords
EnaminonesX-ray diffractionVT-NMRFlexible rotation
Keywords
ENAMINONESBENZOYLACETONECONDENSATIONTAUTOMERISMDERIVATIVESPRODUCTS
ISSN
0022-2860
Abstract
A series of 1-aryl-3-(cyclicamino)-prop-2-en-1-one analogs was synthesized from commercial acetophenones in 2 or 3 steps. Compound 6, (E)-3-(piperidinyl)-1-(2′-hydroxyphenyl)-prop-2-en-1-one, exhibited the unique shape and intensity of the Csp2NCH2peaks in the 1H and 13C NMR spectra. Variable temperature (VT) nuclear magnetic resonance (NMR) and X-ray diffraction (XRD) studies of 6 revealed that the piperidine ring has a lower energy barrier to rotation than the 5-membered pyrrolidine 9 due to the less effective π electron delocalization along the Csp2N bond. © 2014 Elsevier B.V. All rights reserved.
URI
http://hdl.handle.net/20.500.11750/2370
DOI
10.1016/j.molstruc.2014.08.016
Publisher
Elsevier B.V.
Related Researcher
  • 구재형 Koo, JaeHyung
  • Research Interests 장내미생물/감염균 유래 대사체를 통한 신경염증; 알츠하이머병; 우울증; 당뇨/비만; 대사체/수용체 상호작용에 의한 대사연구
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