Carbene →N+ Coordination Bonds in Drugs: A Quantum Chemical Study

Kathuria, Deepika; Arfeen, Minhajul; Aa, Bankar; Bharatam, Prasad V.

doi:10.1007/s12039-016-1173-2

Cited by 23 publications

(12 citation statements)

References 26 publications

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“…L] + , named as nitreones (Scheme 1), [13] has also gained considerable attention. [14][15][16] Akin to the bonding situation of the carbon atom in carbones, the dicoordinated nitrogen(I) atom in nitreones possesses two lone pairs of electrons. Therefore, nitreones differ significantly from those of nitrenium ions [DNR 2 ] + which are isolobal to carbenes.…”

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confidence: 99%

Bis(silylene)‐Stabilized Monovalent Nitrogen Complexes

et al. 2020

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The first series of bis(silylene)-stabilized nitrogen(I) compounds is described. Starting from the 1,2-bis(N-heterocyclic silylenyl) 1,2-dicarba-closo-dedocaborane(12) scaffold 1, [1,2-(LSi) 2 C 2 B 10 H 10 ; L = PhC(N t Bu) 2 ], reaction with adamantyl azide (AdN 3) affords the terminal N-m 2-bridged zwitterionic carborane-1,2-bis(silylium) AdN 3 adduct 2 with an open-cage dianionic nido-C 2 B 10 cluster core. Remarkably, upon one-electron reduction of 2 with C 8 K and liberation of N 2 and adamantane, the two silylene subunits are regenerated to furnish the isolable bis(silylene)-stabilized N I complex as an anion of 3 with the nido-C 2 B 10 cluster cage. On the other hand, one-electron oxidation of 2 with silver(I) yields the monocationic bis(silylene) N I complex 4 with the closo-C 2 B 10 cluster core. Moreover, the corresponding neutral N I radical complex 5 results from single-electron transfer from 3 to 4.

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confidence: 99%

Bis(silylene)‐Stabilized Monovalent Nitrogen Complexes

et al. 2020

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“…NHCs are highly nucleophilic, they can donate electron density to main group elements like carbon, nitrogen etc. and examples are carbones and nitreones [43][44][45][46][47][48][49][50][51][52]. In the series of oximes studied in this work, the oxime center is electron deficient because the C=N-OH center carries a proton.…”

Section: Resultsmentioning

confidence: 98%

“…In this work, quantum chemical analysis has been carried out to explore the electronic structure of a series of cationic oximes (O-1 toO-15 ) and the corresponding NNHOs (O'-1 toO'-15 ) using density functional methods. This work is in continuation of our efforts in exploring the L-N coordination bond in nitreone class of compounds [43][44][45][46][47][48][49][50][51][52]. The chemical bond between the ring systems and the carbon center was explored; the bond dissociation energy of the NHC in these species has been estimated.…”

Section: Introductionmentioning

confidence: 95%

NHC Ligated Oximes: Exploring the Electronic Structure and Properties

Dar¹,

Dubey²,

Singh³

et al. 2021

Preprint

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Compounds with (NHC)→E coordination bond are being generated and their chemistry is being explored over the past 15 years (NHC= N-heterocyclic carbenes, E = main group elements). Many examples of species with N-heterocyclic olefins (NHOs) are known, which exhibit umpolung chemistry. Increasing number of chemical species, which carry NHC as a functional unit, are being reported. There is a need to understand their electronic structure. Alkylated imidazole oximes (cationic, found useful in medicinal chemistry) ((NHC)-C(H)=N-OH(+)) carry NHC unit as a functional group. Similarly, the corresponding nitroso-N-heterocyclic olefins ((NHC)=C(R)-N=O) also carry NHC as a functional unit. It is important to establish the interaction between the NHC unit and the rest part of the molecule in these species. Density functional (DFT) study has been carried out to explore the electronic structure details of a few oximes and nitroso NHOs. The results indicate that a structure with NHC→C coordination interaction can be considered as one of the resonance structures of these species.

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“…In this work, quantum chemical analysis has been carried out to explore the electronic structure of a series of cationic oximes ( O‐1 to O‐15 ) and the corresponding NNHOs ( O′‐1 to O′‐15 ) using density functional methods. This work is in continuation of our efforts in exploring the L → N coordination bond in nitreone class of compounds [43–52].…”

Section: Introductionmentioning

confidence: 85%

N‐heterocyclic carbene ligated oximes: Exploring the electronic structure and properties

Dar

Dubey

Singh

et al. 2022

Int J of Quantum Chemistry

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Compounds with (NHC) → E coordination bond represent a family of chemical species with significant interest and their chemistry is being explored over the past 15 years, where NHC and E represent N‐heterocyclic carbene and main group elements, respectively. NHOs (N‐heterocyclic olefins) are special among these because of the (NHC) → CR2 interaction. NHOs carry nucleophilic exocyclic carbon and many interesting reactions of NHOs are due to this character. Alkylated imidazole oximes (cationic, found useful in medicinal chemistry) [(NHC) → C(H) = NOH]+ carry NHC unit as a functional group. Similarly, the corresponding nitroso‐N‐heterocyclic olefins [(NHC) → C(R)NO] also carry NHC as a functional unit. It is important to establish the interactions between the NHC unit and the rest of the molecule in these species. Density functional theory (DFT) was employed to explore the electronic structure details of a series of oximes and nitroso NHOs. The results indicate that a structure with (NHC) → C coordination interaction can be considered as one of the resonance structures of these species.

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Carbene →N+ Coordination Bonds in Drugs: A Quantum Chemical Study

Cited by 23 publications

References 26 publications

Bis(silylene)‐Stabilized Monovalent Nitrogen Complexes

Bis(silylene)‐Stabilized Monovalent Nitrogen Complexes

NHC Ligated Oximes: Exploring the Electronic Structure and Properties

N‐heterocyclic carbene ligated oximes: Exploring the electronic structure and properties

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