Nguyen Trung Thanh, Le Thach Ngoc, Duus Fritz, Hansen Bjarke K V, Hansen Poul Erik
Department of Organic Chemistry, University of Natural Sciences, National University of HoChiMinh City, 227 Nguyen Van Cu St, Dist 5, HoChiMinh City, Vietnam.
Magn Reson Chem. 2007 Mar;45(3):245-52. doi: 10.1002/mrc.1957.
A new class of compounds, the 2-hydroxythioacetophenones, and related compounds have recently been synthesized. The hydrogen-bond system has been characterized by NMR chemical shifts and deuterium isotope effects on these as well as by DFT calculations. Use of solid-state (13)C NMR has enabled measurements of the intrinsic deuterium isotope effects of the most abundant tautomer of beta-thioxoketones. The compounds show very interesting long-range deuterium isotope effects on the thiocarbonyl carbon. The intramolecular hydrogen bonds of o-hydroxythioacetophenones are found to be slightly stronger than those of the corresponding acetophenones. The reactivity and stability of the compounds can be related to hydrogen bonding and to the presence of electron donating substituents.
最近合成了一类新型化合物，即2-羟基硫代苯乙酮及其相关化合物。通过核磁共振化学位移、这些化合物上的氘同位素效应以及密度泛函理论计算对氢键系统进行了表征。固态(13)C核磁共振的使用使得能够测量β-硫代酮最丰富互变异构体的固有氘同位素效应。这些化合物对硫羰基碳显示出非常有趣的远程氘同位素效应。发现邻羟基硫代苯乙酮的分子内氢键比相应苯乙酮的分子内氢键略强。这些化合物的反应性和稳定性与氢键以及给电子取代基的存在有关。
