NO-induced adaptive antiaromaticity in cyclobutadiene

Deng, Qianqian; Imran, Sajid; Yan, Jun; Zhu, Jun

doi:10.1039/d3qo01498c

Org. Chem. Front.

2023

DOI: 10.1039/d3qo01498c

|View full text |Cite

NO-induced adaptive antiaromaticity in cyclobutadiene

Qianqian Deng,

Sajid Imran,

Jun Yan

et al.

Abstract: Cyclobutadiene (CBD) displays aromaticity in the lowest-lying triplet excited state (T1) according to the Baird's 4n electron rule. Hence, antiaromatic CBD in the T1 state has never been reported so...

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2024

Publication Types

Select...

Article1

Relationship

Self Cite1

Independent0

Authors

Journals

Cited by 1 publication

References 80 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Probing σ-Aromaticity-Driven Ring Contraction of Metallabenzocyclobutadiene to Metallabenzocyclopropene

Xing,

Tan,

Zhu

2024

Inorg. Chem.

Self Cite

View full text Add to dashboard Cite

Ring contraction of metallacyclobutadiene to metallacyclopropene is rare because of the increasing strain from a four-membered ring to a three-membered one. Here we demonstrate a new series of reactions of metallabenzocyclobutadiene to metallabenzocyclopropene via density functional theory calculations. The results suggest that these reactions are thermodynamically favorable ranging from −17.4 to −29.4 kcal mol −1 , and a low reaction barrier (10.3 kcal mol −1 ) is achieved when the metal center is Ru and the ligands are one cyanide and one chloride. Further analysis suggests that a strengthened binding energy helps stabilize the transition state in the protonation process. The aromaticity during the reaction was investigated using the electron density of delocalized bonds (EDDB), isomerization stabilization energy, and isodesmic reactions. The EDDB shows that the π-conjugation is disrupted in the intermediate, and then σ-aromaticity is generated and dominant in the products. Our findings could be helpful for experimentalists in developing novel ring contraction reactions driven by aromaticity.

show abstract

Probing σ-Aromaticity-Driven Ring Contraction of Metallabenzocyclobutadiene to Metallabenzocyclopropene

Xing,

Tan,

Zhu

2024

Inorg. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

NO-induced adaptive antiaromaticity in cyclobutadiene

Abstract: Cyclobutadiene (CBD) displays aromaticity in the lowest-lying triplet excited state (T1) according to the Baird's 4n electron rule. Hence, antiaromatic CBD in the T1 state has never been reported so...

Cited by 1 publication

References 80 publications

Probing σ-Aromaticity-Driven Ring Contraction of Metallabenzocyclobutadiene to Metallabenzocyclopropene

Probing σ-Aromaticity-Driven Ring Contraction of Metallabenzocyclobutadiene to Metallabenzocyclopropene

Contact Info

Product

Resources

About