Acyclic Twisted Amides

Guangrong Meng; Jin Zhang; Michal Szostak

doi:10.1021/acs.chemrev.1c00225

Acyclic Twisted Amides

Guangrong Meng, Jin Zhang, Michal Szostak

Rutgers Newark, Chemistry

Research output: Contribution to journal › Review article › peer-review

116 Scopus citations

Abstract

In this contribution, we provide a comprehensive overview of acyclic twisted amides, covering the literature since 1993 (the year of the first recognized report on acyclic twisted amides) through June 2020. The review focuses on classes of acyclic twisted amides and their key structural properties, such as amide bond twist and nitrogen pyramidalization, which are primarily responsible for disrupting nN to π*C= conjugation. Through discussing acyclic twisted amides in comparison with the classic bridged lactams and conformationally restricted cyclic fused amides, the reader is provided with an overview of amidic distortion that results in novel conformational features of acyclic amides that can be exploited in various fields of chemistry ranging from organic synthesis and polymers to biochemistry and structural chemistry and the current position of acyclic twisted amides in modern chemistry.

Original language	English (US)
Pages (from-to)	12746-12783
Number of pages	38
Journal	Chemical Reviews
Volume	121
Issue number	20
DOIs	https://doi.org/10.1021/acs.chemrev.1c00225
State	Published - Oct 27 2021

All Science Journal Classification (ASJC) codes

General Chemistry

Access to Document

10.1021/acs.chemrev.1c00225

Cite this

@article{9e4ce694eb0f4417a2c0596c98debec2,

title = "Acyclic Twisted Amides",

abstract = "In this contribution, we provide a comprehensive overview of acyclic twisted amides, covering the literature since 1993 (the year of the first recognized report on acyclic twisted amides) through June 2020. The review focuses on classes of acyclic twisted amides and their key structural properties, such as amide bond twist and nitrogen pyramidalization, which are primarily responsible for disrupting nN to π*C= conjugation. Through discussing acyclic twisted amides in comparison with the classic bridged lactams and conformationally restricted cyclic fused amides, the reader is provided with an overview of amidic distortion that results in novel conformational features of acyclic amides that can be exploited in various fields of chemistry ranging from organic synthesis and polymers to biochemistry and structural chemistry and the current position of acyclic twisted amides in modern chemistry.",

author = "Guangrong Meng and Jin Zhang and Michal Szostak",

note = "Funding Information: Rutgers University, the NSF (CAREER CHE-1650766), and the NIH (1R35GM133326) are gratefully acknowledged for support. J.Z. thanks the China Scholarship Council (201808610096). Additional support was provided by the Rutgers Graduate School in the form of Dean{\textquoteright}s Dissertation Fellowship (G.M.). Publisher Copyright: {\textcopyright} 2021 American Chemical Society. All rights reserved.",

year = "2021",

month = oct,

day = "27",

doi = "10.1021/acs.chemrev.1c00225",

language = "English (US)",

volume = "121",

pages = "12746--12783",

journal = "Chemical Reviews",

issn = "0009-2665",

publisher = "American Chemical Society",

number = "20",

}

TY - JOUR

T1 - Acyclic Twisted Amides

AU - Meng, Guangrong

AU - Zhang, Jin

AU - Szostak, Michal

N1 - Funding Information: Rutgers University, the NSF (CAREER CHE-1650766), and the NIH (1R35GM133326) are gratefully acknowledged for support. J.Z. thanks the China Scholarship Council (201808610096). Additional support was provided by the Rutgers Graduate School in the form of Dean’s Dissertation Fellowship (G.M.). Publisher Copyright: © 2021 American Chemical Society. All rights reserved.

PY - 2021/10/27

Y1 - 2021/10/27

N2 - In this contribution, we provide a comprehensive overview of acyclic twisted amides, covering the literature since 1993 (the year of the first recognized report on acyclic twisted amides) through June 2020. The review focuses on classes of acyclic twisted amides and their key structural properties, such as amide bond twist and nitrogen pyramidalization, which are primarily responsible for disrupting nN to π*C= conjugation. Through discussing acyclic twisted amides in comparison with the classic bridged lactams and conformationally restricted cyclic fused amides, the reader is provided with an overview of amidic distortion that results in novel conformational features of acyclic amides that can be exploited in various fields of chemistry ranging from organic synthesis and polymers to biochemistry and structural chemistry and the current position of acyclic twisted amides in modern chemistry.

AB - In this contribution, we provide a comprehensive overview of acyclic twisted amides, covering the literature since 1993 (the year of the first recognized report on acyclic twisted amides) through June 2020. The review focuses on classes of acyclic twisted amides and their key structural properties, such as amide bond twist and nitrogen pyramidalization, which are primarily responsible for disrupting nN to π*C= conjugation. Through discussing acyclic twisted amides in comparison with the classic bridged lactams and conformationally restricted cyclic fused amides, the reader is provided with an overview of amidic distortion that results in novel conformational features of acyclic amides that can be exploited in various fields of chemistry ranging from organic synthesis and polymers to biochemistry and structural chemistry and the current position of acyclic twisted amides in modern chemistry.

UR - http://www.scopus.com/inward/record.url?scp=85114190964&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85114190964&partnerID=8YFLogxK

U2 - 10.1021/acs.chemrev.1c00225

DO - 10.1021/acs.chemrev.1c00225

M3 - Review article

C2 - 34406005

AN - SCOPUS:85114190964

SN - 0009-2665

VL - 121

SP - 12746

EP - 12783

JO - Chemical Reviews

JF - Chemical Reviews

IS - 20

ER -

Acyclic Twisted Amides

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this