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X-ray diffraction and VT-NMR studies of (E)-3-(piperidinyl)-1-(2 '-hydroxyphenyl)-prop-2-en-1-one
- Authors
- Choi, Seunghyun; Kim, YunHye; Park, Bernie Byeonghoon; Park, Suzie; Park, Jonghyun; Ok, Kiwon; Koo, JaeHyung; Jung, Yong Woo; Jeon, Young Ho; Lee, Eun Hee; Lee, Ken S.; Byun, Youngjoo
- Issue Date
- 5-11월-2014
- Publisher
- ELSEVIER
- Keywords
- Enaminones; X-ray diffraction; VT-NMR; Flexible rotation
- Citation
- JOURNAL OF MOLECULAR STRUCTURE, v.1076, pp.600 - 605
- Indexed
- SCIE
SCOPUS
- Journal Title
- JOURNAL OF MOLECULAR STRUCTURE
- Volume
- 1076
- Start Page
- 600
- End Page
- 605
- 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 C-sp2-N-CH2 peaks in the H-1 and C-13 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 pi electron delocalization along the C-sp2-N bond. (C) 2014 Elsevier B.V. All rights reserved.
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