2-α-hydroxybenzhydryl- and 2,7-di(α-hydroxybenzhydryl)-1,8-bis(dimethylamino)naphthalenes:: the first examples of stabilization of in/out proton sponge conformers by intramolecular hydrogen bonding.: The most flattened amino group ever participating in IHB

被引:19
作者
Pozharskii, AF
Ryabtsova, OV
Ozeryanskii, VA
Degtyarev, AV
Starikova, ZA
Sobczyk, L
Filarowski, A
机构
[1] Rostov State Univ, Dept Chem, Rostov Na Donu 344090, Russia
[2] Russian Acad Sci, AN Nesmeyanov Organomet Cpds Inst, Moscow 119991, Russia
[3] Univ Wroclaw, Fac Chem, PL-50383 Wroclaw, Poland
基金
俄罗斯基础研究基金会;
关键词
D O I
10.1016/j.tetlet.2005.04.045
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-(alpha-Hydroxybenzhydryl)-6 and 2,7-di(alpha-hydroxybenzhydryl)-1,8-bis(dimethylamino)naphthalenes 8 have been shown to exist in crystals as in/out conformers stabilized by O-H center dot center dot center dot N intramolecular hydrogen bonding. In agreement with X-ray studies, the NMR data are also consistent with 7 retaining its in/out form in solution, whilst for 8 superimposed equilibrating in/out out/in conformers are observed. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3973 / 3976
页数:4
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