N-フェニルチオウレタンの水素結合

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A quantitative infrared spectroscopic study of a model thiourethane-type compound was carried out in order to obtain basic data on hydrogen bonding in polythiourethanes. First, the integrated molar absorption coefficient (A) and the peak-hight molar absorption coefficient (ε) of stretching vibrations of free N-H groups of N-phyenylthiourethane (PhT), which was adopted as the model thiourethane, were determined by Wilson-Wells' method and the peak-height method, respectively, on the assumption that the coefficients of trans and cis N-H groups are equal. The values of A and ε were 4.61×103 l./mole-cm2. and 2.38×203 l./mole-cm.. The free N-H groups of PhT absorbed at 3418 cm-1. (trans) and 3393 cm-1. (cis), and hydrogen-bonded N-H ones at 3223 cm-1. (trans-trans), at 3180 cm-1 (cis-cis) and at 3120 cm-1. (trans-cis), respectively. Then, the extents of hydrogen bonding of PhT at various concentrations were determined, and hydrogen bonding between PhT and ethers were studied by using the above-mentioned coefficients. The equilibrium constant of self-association of PhT was 9.39 (based on A) or 12.2 l./mokr(based on ε). Di-n-butyl ether (DBE) and poly (oxyethylene glycol) (PEG) were examined and proved to be able to act as proton acceptors. The frequency shift of N-H stretching vibration of PhT caused by hydrogen bonding with PEG was 156 cm-1. (trans N-H…-0-). The equilibrium constants were 1.43 (PhT-DBE) and 3.62 l./mole (PhT-PEG), respectively. The stronger hydrogen bonding ability of polyether was explained in terms of local concentrating effect. The results were discussed in connection with those of urethanes.
長崎大学工学部,Faculty of Engineering, Nagasaki Universityの論文

N-フェニルチオウレタンの水素結合

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