![1-{3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl}-2,3-dihydroxy-1-propanone structure](https://static.chemtradehub.com/structs/122/1226872-27-0-e037.webp "1-{3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl}-2,3-dihydroxy-1-propanone structure")
1-{3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl}-2,3-dihydroxy-1-propanone
CAS Number:
1226872-27-0
Molecular Formula:
C25H26N6O4
NO-induced adaptive antiaromaticity in cyclobutadiene
Literature Information
Publication Date
2023-10-23
DOI
10.1039/D3QO01498C
Impact Factor
5.281
Authors
Qianqian Deng, Sajid Imran, Jun Yan, Jun Zhu
View Original
Abstract
Cyclobutadiene (CBD) displays aromaticity in the lowest-lying triplet excited state (T1) according to Baird's 4n electron rule. Hence, antiaromatic CBD in the T1 state has never been reported so far. Here we demonstrate via density functional theory (DFT) calculations that the CBD ring could possess dual antiaromaticity in the lowest singlet state (S0) and T1 states (termed as adaptive antiaromaticity), which is supported by various aromaticity indices including NICS, ACID, ΔBL, ELF and ISE. Furthermore, the spin density localization on the substituent is the key factor for NO-substituted CBD to maintain antiaromaticity in the T1 state. The principal interacting spin orbital (PISO) analysis suggests that the nitrogen atom in the NO substituent tends to form a double bond with the carbon atom in the CBD ring, blocking the delocalization into the CBD ring and resulting in the antiaromaticity in the T1 state. Our findings represent a step forward in aromatic chemistry.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
1-Isobutyl-7-methoxy-2,3,4,9-tetrahydro-1H-beta-carboline
CAS Number:
175975-76-5
Molecular Formula:
C16H22N2O
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