受四键相互作用的影响，脯氨酰氨基甲酸酯中的顺式PR稳定。

IF 4.6 Q2 MATERIALS SCIENCE, BIOMATERIALS

ACS Applied Bio Materials Pub Date : 2024-10-28 DOI:10.1039/d4ob01539h

Shreya Banerjee, Shama Tumminakatti, Sudip Ghosh, Vamsee K Voora, Erode N Prabhakaran

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引用次数: 0

摘要

对同源脯氨酰氨基甲酸酯的核磁共振光谱和理论分析揭示了微妙的电荷转移四键相互作用（TBI），选择性地稳定了它们的顺式 Pro 转子。这些 TBI 涉及 C 端酰胺到 N 端氨基甲酸酯羰基-羰基（n → π* 型），然后是氨基甲酸酯内部（n → σ* 型）的电荷转移相互作用，这些相互作用完全发生在 cisPro 主题中。TBI 的数量以及 cisPro 的稳定性随着氨基甲酸乙酯上 Cβ 基团数量的增加而增加。溶剂极性的增加也会提高顺式 Pro 氨基甲酸酯的相对稳定性。

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cisPro stabilization in prolyl carbamates influenced by tetrel bonding interactions.

NMR spectral and theoretical analyses of homologous prolyl carbamates reveal subtle charge transfer tetrel bonding interactions (TBIs), selectively stabilizing their cisPro rotamers. These TBIs involve C-terminal-amide to N-terminal carbamate carbonyl-carbonyl (n → π* type) followed by intra-carbamate (n → σ* type) charge transfer interactions exclusively in the cisPro motif. The number of TBIs and hence the cisPro stability increase with increasing number of C^β groups at the carbamate alcohol. Increasing solvent polarities also increase the relative cisPro carbamate stabilities.

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来源期刊

ACS Applied Bio Materials Chemistry-Chemistry (all)

CiteScore

9.40

自引率

2.10%

发文量

464