Journal of the Chemical Society. Perkin transactions II p. 387 - 392 (1991)
Update date:2022-08-23
Topics:
Parmentier, J.
Samyn, C.
Beylen, M. Van
Zeegers-Huyskens, Th.
FT-IR spectra of N-t-butoxycarbonylglycine-N',N'-dimethylamide and its deuteriated ND counterpart, in solution and in the solid state, have been analysed between 3800 and 400 cm-1.An assignment is proposed for some important vibrations, especially for the so-called amide vibrations, by comparison with literature data on similar molecules.The frequency shifts and intensity changes of the vibrations sensitive to the physical state of this model dipeptide strongly suggest that intermolecular hydrogen bonds involving mainly the NH and C=O (amide) groups are formed in the solid state.Thermodynamic parameters (equilibrium constants and enthalpies) of the hydrogen-bond formation with phenol derivatives have been determined in carbon tetrachloride and in 1,2-dichloroethane.The complexes investigated are of medium strength.The FT-IR spectra in the νC=O region and the double perturbation of the νNH band assigned to the five-membered intramolecular NH...O=C hydrogen-bonded ring clearly show that complex formation occurs at both the amide and urethane carbonyl groups.About 45percent of the complexes are formed on the C=O (urethane) function, almost independent of the acidity of the phenols.The unusual broadness of the OH...O=C complex band originates from the superposition of two complex bands.N-t-Butoxycarbonylglycine-N',N'-dimethylamide can be considered as being built up from two model molecules, methyl-N-methylcarbamate and N,N-dimethylacetamide.
View MoreCangzhou Senary Chemical Science-tech Co., Ltd
Contact:+86-317-3563899, 3563699
Address:168 Jinde Road, Cangzhou, Hebei, China
Contact:+86-571-87859231, 87859237, 87859239
Address:1606,Huarong Times Mansion, No.3880 Jiangnan Avenue, Binjiang District, Hangzhou, China, 310053
Jiangsu Fengshan Group Co., Ltd.
Contact:86-25-86558671
Address:1903,Central International Mansion 105-6 North Zhongshan Road, Nanjing, China
WUXI HONOR SHINE CHEMICAL CO.,LTD
Contact:+86-510-83593312
Address:No.1699 Huishan avenue,Huishan district,Wuxi ,Jiangsu,China,214177.(Wuxi Huishan Ecomonic Develop Zone )
Contact:+86-710-3516804
Address:Number 83,Panggong road,Xiangcheng District,Xiangyang ,Hubei
Doi:10.1039/c5ra07983g
(2015)Doi:10.1007/BF01517100
(1880)Doi:10.1515/hc-2012-0174
(2013)Doi:10.1016/j.tetlet.2007.09.035
(2007)Doi:10.1016/j.tetlet.2019.03.022
(2019)Doi:10.1021/ja0351591
(2003)
