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揭示含丙二酸大环化合物在酸性pH下的脱羧反应：一种被忽视现象的影响及应用

Unveiling the Decarboxylation of a Malonic Acid-Containing Macrocycle at Acidic pH: Implications and Applications of an Overlooked Phenomenon.

作者信息

Franchi Sara, Tosato Marianna, Di Marco Valerio

机构信息

Department of Chemical Sciences, University of Padova, 35131, Padova, Italy.

Radiopharmaceutical Chemistry Laboratory, Nuclear Medicine Unit, AUSL-IRCCS Reggio Emilia, 42123, Reggio Emilia, Italy.

出版信息

Chempluschem. 2025 Aug;90(8):e202500213. doi: 10.1002/cplu.202500213. Epub 2025 Jun 10.

DOI:10.1002/cplu.202500213
PMID:40407315
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12352729/
Abstract

1,10-Diaza-18-crown-6-1,10-bis(malonic acid) (oddm or macromal) is a promising chelator for large hard metal cations due to its unique structure, which combines the complexing properties of aza-crown Kryptofix 22 with those of malonic acid. This study uncovers the previously overlooked decarboxylation of macromal under mildly to strongly acidic pH conditions at room temperature. As a result, the acidity constants of macromal are carefully re-evaluated, providing precise data for its accurate and informed handling in aqueous media. The implications of these findings for metal complexation and new possible applications of macromal are also presented.

摘要

1,10-二氮杂-18-冠-6-1,10-双（丙二酸）（oddm或macromal）因其独特的结构，将氮杂冠醚穴状配体22的络合特性与丙二酸的络合特性相结合，是一种用于大的硬金属阳离子的有前景的螯合剂。本研究揭示了在室温下，macromal在弱酸性至强酸性pH条件下先前被忽视的脱羧反应。结果，对macromal的酸度常数进行了仔细的重新评估，为其在水性介质中的准确和明智处理提供了精确数据。还介绍了这些发现对金属络合的影响以及macromal新的可能应用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e9f/12352729/5cd5f12f9073/CPLU-90-e202500213-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e9f/12352729/56bd8b2d7f51/CPLU-90-e202500213-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e9f/12352729/2097fdfe2553/CPLU-90-e202500213-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e9f/12352729/f7be71352a7e/CPLU-90-e202500213-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e9f/12352729/073982eed46b/CPLU-90-e202500213-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e9f/12352729/f377d1f66af3/CPLU-90-e202500213-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e9f/12352729/555564d167af/CPLU-90-e202500213-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e9f/12352729/5cd5f12f9073/CPLU-90-e202500213-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e9f/12352729/56bd8b2d7f51/CPLU-90-e202500213-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e9f/12352729/2097fdfe2553/CPLU-90-e202500213-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e9f/12352729/f7be71352a7e/CPLU-90-e202500213-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e9f/12352729/073982eed46b/CPLU-90-e202500213-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e9f/12352729/f377d1f66af3/CPLU-90-e202500213-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e9f/12352729/555564d167af/CPLU-90-e202500213-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5e9f/12352729/5cd5f12f9073/CPLU-90-e202500213-g002.jpg

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