化学学报 ›› 1963, Vol. 29 ›› Issue (5): 361-363. 上一篇    下一篇

研究简报

N-环已烷氨基乙酸和N-β-萘氨基乙酸的离解常数

陈荣悌, 纪柱, 徐孔钰   

  1. 南开大学化学系
  • 投稿日期:1962-10-26 发布日期:2013-06-03

THE DISSOCIATION CONSTANTS OF N-CYCLOHEXYLGLYCINE AND N-β-NAPHTHYLGLYCINE

CHEN YUN-TI, CHI CHU, HSÜ KUNG-YÜ   

  1. Department of Chemistry, Nankai University
  • Received:1962-10-26 Published:2013-06-03

在25°及0.10M高氯酸鈉存在下, N-环己烷氨基乙酸(CyG)和N-β-萘氨基乙酸(βNG)在30%(体积)乙醇中的表观离解常数用pH法測定为:CyG:pKCOOH=2.70, pKR2NH2+=9.83;βNG:pKCOOH=2.26, pXR2NH2+=4.46.前者(CyG)的酸碱強度均与氨基乙酸(G)的相似, 但后者(βNG)的碱性却小于其异构体N-α-萘氨基乙酸(αNG)的碱性約百万倍, 而与N-苯氨基乙酸(φG)的碱性相似.这进一步說明αNG上的8位氫原子和1位上羧甲氨基之間的空間效应是导致其碱性增強的主要原因.βNG的酸性較αNG略強, 可能是在共軛程度較高的βNG分子中, N的电子密度較低的β-萘氨基对于羧基所产生較大的誘导效应之結果.

The apparent acid dissociation constants of N-cyclohexylglycine and N-β-naphthyl-glycine have been determined to be PKCOOH=2.70, PKR3NH3+=9.83 for the former and PKCOOH=2.26, PKR3NH3+=4.46 for the later by pH method at 25° in 30% ethanol solution in the presence of 0.10M sodium perchlorate.It was found that N-cyclohexyl-glycine as a base is comparable to that of glycine and N-alkylglycines, as expected, while the basicity of N-β-naphthylglycine is quite different from that of its isomer, N-α-naphthylglycine.These results evidently support our previous interpretation on the abnormally high basicity of N-α-naphthylglycine that steric effect due to the 8-hydrogen on the naphthalene ring upon the proton on the amino group was responsible for such an anomaly.