Urea vs. thiourea in anion recognition

Urea vs. thiourea in anion recognition
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DOI:
10.1039/b500123d
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发表时间:
2005-01-01
影响因子:
3.2
通讯作者:
Monzani, E
Monzani, E
中科院分区:
化学3区
文献类型:
--
作者:
Gómez, DE;Fabbrizzi, L;Monzani, E

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中性阴离子受体(LH)与羧酸盐、卤化物和磷酸盐(X-)形成稳定的1:1氢键[LH中心点中心点X](-)复合物。某些[LH中心点X](-)复合物在过量X-存在下释放HX片段,形成[HX 2](-)和去质子化受体L-。去质子化的趋势随着受体的酸度和[HX 2](-)自身络合物的稳定性而增加。因此,含硫脲的受体在除氯离子以外的所有研究阴离子存在下去质子化,而含脲的受体由于[HF 2](-)的高稳定性仅在氟离子存在下经历去质子化。
Neutral anion receptors (LH) form stable 1 : 1 H-bond [LH center dot center dot center dot X](-) complexes with carboxylates, halides and phosphate (X-). Some of the [LH center dot center dot center dot X](-) complexes, in presence of an excess of X-, release an HX fragment, with formation of [HX2](-) and the deprotonated receptor L-. The tendency towards deprotonation increases with the acidity of the receptor and with the stability of the [HX2](-) self-complex. Thus, the more acidic thiourea containing receptor deprotonates in the presence all the investigated anions except chloride, whereas the less acidic urea containing receptor undergoes deprotonation only in the presence of fluoride, due to the high stability of [HF2](-).