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Investigation of the demetallation of 10-aryl substituted synthetic chlorins under acidic conditions.
Journal of Inorganic Biochemistry ( IF 3.8 ) Pub Date : 2020-01-03 , DOI: 10.1016/j.jinorgbio.2019.110979 Anna I Arkhypchuk 1 , Ruisheng Xiong 1 , K Eszter Borbas 1
Journal of Inorganic Biochemistry ( IF 3.8 ) Pub Date : 2020-01-03 , DOI: 10.1016/j.jinorgbio.2019.110979 Anna I Arkhypchuk 1 , Ruisheng Xiong 1 , K Eszter Borbas 1
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The acidic demetallation of a series of sparsely substituted Zn(II) chlorins is reported. The chlorins were functionalized in the 10-position with substituents ranging from strongly electron donating mesityl and p-methoxyphenyl to electron-withdrawing p-nitrophenyl and pentafluorophenyl groups. The demetallation kinetics were investigated using UV-Visible absorption spectroscopy. Demetallation was carried out by exposing the metallochlorins dissolved in CH2Cl2 to an excess of trifluoroacetic acid. Reasonable correlation was found between the Hammett constant of the 10-substituent and the rate constant of the loss of the metal ion. The largest differences were observed between the p-methoxyphenyl and p-nitrophenyl-substituted Zn(II) chlorins, undergoing loss of Zn(II) with pseudo first order rate constants of 0.0789 × 10-3 and 3.70 × 10-3 min-1, respectively. Taken together, these data establish the dramatic influence even subtle changes can have in altering the electronic properties of chlorins, which in turn impacts metallochlorin function.
中文翻译：
在酸性条件下研究10-芳基取代的合成二氢卟酚的脱金属作用。
报告了一系列稀疏取代的Zn（II）二氢卟酚的酸性脱金属。二氢卟酚在10位上被取代基官能化，取代基的范围从强电子给体基和对甲氧基苯基到吸电子对硝基苯基和五氟苯基。使用UV-可见吸收光谱法研究了脱金属动力学。通过将溶解在CH2Cl2中的金属氯盐暴露于过量的三氟乙酸中进行脱金属。在10位取代基的哈米特常数和金属离子损失的速率常数之间发现了合理的相关性。在对甲氧基苯基和对硝基苯基取代的Zn（II）二氢卟酚之间观察到最大的差异，Zn（II）的损失具有伪一级速率常数0.0789×10-3和3.70×10-3 min-1 ，分别。总之，这些数据建立了巨大的影响，即使微妙的变化也会改变二氢卟酚的电子特性，进而影响金属氯霉素的功能。
更新日期：2020-01-04
中文翻译：
在酸性条件下研究10-芳基取代的合成二氢卟酚的脱金属作用。
报告了一系列稀疏取代的Zn（II）二氢卟酚的酸性脱金属。二氢卟酚在10位上被取代基官能化，取代基的范围从强电子给体基和对甲氧基苯基到吸电子对硝基苯基和五氟苯基。使用UV-可见吸收光谱法研究了脱金属动力学。通过将溶解在CH2Cl2中的金属氯盐暴露于过量的三氟乙酸中进行脱金属。在10位取代基的哈米特常数和金属离子损失的速率常数之间发现了合理的相关性。在对甲氧基苯基和对硝基苯基取代的Zn（II）二氢卟酚之间观察到最大的差异，Zn（II）的损失具有伪一级速率常数0.0789×10-3和3.70×10-3 min-1 ，分别。总之，这些数据建立了巨大的影响，即使微妙的变化也会改变二氢卟酚的电子特性，进而影响金属氯霉素的功能。
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