(2S,4R)-4-Hydroxyproline(4-nitrobenzoate): Strong Induction of Stereoelectronic Effects via a Readily Synthesized Proline Derivative. Crystallographic Observation of a Correlation betwee

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• 作者：Anil K. Pandey ; Glenn P. A. Yap ; Neal J. Zondlo
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：May 2, 2014
• 年：2014
• 卷：79
• 期：9
• 页码：4174-4179
• 全文大小：331K
• 年卷期：v.79,no.9(May 2, 2014)
• ISSN：1520-6904

文摘

(2S,4R)-4-Hydroxyproline(4-nitrobenzoate) was synthesized. The crystal structure revealed an exo ring pucker, with the nitrobenzoate pseudoaxial on the pyrrolidine envelope and antiperiplanar to C^尾 and C^未 C鈥揌 bonds. The unit cell exhibited variation in C^未鈥揌/C^纬鈥揙 and C^尾鈥揌/C^纬鈥揙 torsion angles, with a 15掳 increase in torsion angle (148掳 to 163掳) observed to result in a 0.018 脜 decrease in C^未鈥揌/C^纬鈥揙 bond length, consistent with favorable 蟽_C鈥揌 鈫?蟽*_C鈥揙 hyperconjugative interactions increasing with greater orbital overlap.