Larger Substituents Enhance Stereospecificity in 1,1-Diazene Nitrogen Extrusion through Attenuation of Dynamic Mismatching.

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Article in JACS Au, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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5 · Who and what money

Authors and funding

3 authors.

Rong-Kai WuCenter of Chemistry for Frontier Technologies, Department of Chemistry, State Key Laboratory of Clean Energy Utilization, Zhejiang University, Hangzhou 310027, China.

Shuo-Qing ZhangCenter of Chemistry for Frontier Technologies, Department of Chemistry, State Key Laboratory of Clean Energy Utilization, Zhejiang University, Hangzhou 310027, China.ORCID https://orcid.org/0000-0002-7617-3042

Xin HongCenter of Chemistry for Frontier Technologies, Department of Chemistry, State Key Laboratory of Clean Energy Utilization, Zhejiang University, Hangzhou 310027, China.ORCID https://orcid.org/0000-0003-4717-2814

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Dynamic effects represent a crucial mechanism governing the stereoselectivity of nitrogen extrusion from 1,1-diazenes. Elucidating this dynamic behavior provides a mechanistic basis for enhancing nitrogen deletion selectivity. Using pyrrolidine ring contraction as a model reaction, we demonstrate how nitrogen extrusion dynamics control reaction selectivity. Quasiclassical dynamics trajectory simulations reveal that reaction selectivity is dynamically controlled: retention products predominate (60.1% of trajectories) while inversion products are significantly disfavored (3.7%). Mechanistic analysis reveals dynamic mismatching between ring-expansion motion and retention bonding in nitrogen extrusion. Incorporation of the sterically demanding 1-adamantyl substituent effectively promotes retention bonding, attenuates dynamic mismatching, and increases retention products to 79.0%. These results provide mechanistic insight into 1,1-diazene nitrogen extrusion and establish a foundation for rational design of more selective nitrogen deletion reactions.

Indexed as

1,1-diazene nitrogen extrusiondynamic mismatchingpost-transition-state dynamicsquasiclassical dynamics trajectory simulationsstereoselectivity

Identifiers

PMID41755862

DOI10.1021/jacsau.5c01603

PMCPMC12933333

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.