Synthesis of azadiphosphiridine complexes. Theoretical studies on ring formation, the P-to-P′ metal shift and the resulting nitrogen geometry

Schmer, Alexander; Alcaraz, Antonio García; Kyri, Andreas Wolfgang; Schnakenburg, Gregor; Ferao, Arturo Espinosa; Streubel, Rainer

doi:10.1039/d1dt04252a

Cited by 2 publications

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“…[20] In case of tripnictogeniranes, only the RSE for the all cis trimethyl-substituted derivative of azadiphosphiridine kPpentacarbonyltungsten(0) complex (20.98 kcal/mol) was recently reported. [21] Herein, reference RSE data for parent PnX 2 rings 1-4 El (PnEl 2 for short, if only the heavy atoms forming the rings are used for naming) (Figure 2) are reported, as well as an analysis of the factors affecting them. In addition, the previously reported additive estimation method for RSE is further refined by employing a wider set of rings and extended to the use of PnÀ El bond strain contributions (B Pn-El ) that were unavailable beforehand.…”

Section: Introductionmentioning

confidence: 99%

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Ring Strain Energy of Diheteropnictogeniranes El₂Pn (Pn=N, P, As, Sb)– Accurate versus Additive Approaches

Espinosa Ferao,

Rey Planells

2023

Chemistry A European J

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Accurate ring strain energy (RSE) values for sixty‐six parent pnictogeniranes having two other identical p‐block elements, El2Pn, have been reported. A decrease in RSE was observed to correlate with an increase in the p character of the AO used in endocyclic bonds, which is particularly remarkable on descending the groups 15 and 16. The latter also parallels higher ‐NICS(1) values, which seems not to be related with an increase in aromaticity, as pointed out by other NICS‐related criteria, but to atom‐centred diatropic currents mostly arising from the presence of lone pairs. Only in case of pnictogenaditrieliranes Tr2Pn (Tr=B, Al, Ga), the decrease of ‐NICS(1) is related to a lower Hückel‐type 2π‐electron aromaticity on descending group 13. The use of an additive methodology based on atom‐strain contributions enables estimation of RSEs for a large majority of all possible three‐membered rings containing group 13–16 elements with modest accuracy (RMSE=4.371 kcal/mol), that could be remarkably improved by using bond‐strain contributions (RMSE=1.183 kcal/mol) instead.

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Section: Introductionmentioning

confidence: 99%

“…In case of tripnictogeniranes, only the RSE for the all cis trimethyl‐substituted derivative of azadiphosphiridine κ P ‐pentacarbonyltungsten(0) complex (20.98 kcal/mol) was recently reported [21] …”

Section: Introductionmentioning

confidence: 99%

Ring Strain Energy of Diheteropnictogeniranes El₂Pn (Pn=N, P, As, Sb)– Accurate versus Additive Approaches

Espinosa Ferao,

Rey Planells

2023

Chemistry A European J

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Synthesis of Pincer type carbene and their Ag(I)-NHC complexes, and their Antimicrobial activities

Türkyılmaz

Ateş

2022

Journal of Sustainable Construction Materials and Technologies

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In this study, theophylline (1) compounds were synthesized with addition of 2-bromoetha-nol, 2-bromoacetamide and methyl-2-bromoacetate to attain symmetric connections to NHCs (2a–c). New complexes containing the symmetric N-heterocyclic carbene (NHC) ligands were synthesized using azolium salts in dimethyl formamide (DMF). After the NHC predecessor compounds reacted with Ag2O, Ag(I)-NHC complexes were synthesized in the following: 7,9-di-(2-hydroxyethyl)-8,9-dihydro-1,3-dimethyl-1H-purine-2,6(3H,7H)-dionedium silver(I)bromide (3a), 7,9-di(acetamide)-8,9-dihydro-1,3-dimethyl-1H-purine-2,6(3H,7H)-di-ondium silver(I)bromide (3b) and 7,9-di(methylacetate)-8,9-dihydro-1,3-dimethyl-1H-pu-rine-2,6(3H,7H)-diondiumsilver(I)bromide (3c). Both synthesized NHC predecessors (2a-c) and Ag(I)-NHC complexes (3a-c) were described by FTIR, 1H-NMR, 13C-NMR, liquid and solid-state conductivity values, TGA analysis, melting point analysis and XRD spectroscopy. In-vitro antibacterial activities of NHC-predecessors and Ag(I)-NHC complexes were tested against gram-positive bacteria (Staphylococcus Aureus and Bacillus Cereus), gram-negative bacteria (Escherichia Coli and Listeria Monocytogenes), and fungus (Candida Albicans) in Tryptic Soy Broth method. Ag(I)-NHC complexes showed higher antibacterial activity than pure NHC predecessors. The lowest microbial inhibition concentration (MIC) value of compound 3a was obtained as 11.56 μg/ml for Escherichia Coli and 11.52 μg/ml for Staphylococcus Aureus. All tested complexes displayed antimicrobial activity with different results.

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Synthesis of azadiphosphiridine complexes. Theoretical studies on ring formation, the P-to-P′ metal shift and the resulting nitrogen geometry

Abstract: A set of azadiphosphiridine complexes 3a and 4b,c were synthesized in high selectivity using N-H and P-H deprotonation as key steps and RPCl2 as substrates (R = NiPr2 (a), -tBu...

Cited by 2 publications

References 24 publications

Ring Strain Energy of Diheteropnictogeniranes El₂Pn (Pn=N, P, As, Sb)– Accurate versus Additive Approaches

Ring Strain Energy of Diheteropnictogeniranes El₂Pn (Pn=N, P, As, Sb)– Accurate versus Additive Approaches

Synthesis of Pincer type carbene and their Ag(I)-NHC complexes, and their Antimicrobial activities

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Synthesis of azadiphosphiridine complexes. Theoretical studies on ring formation, the P-to-P′ metal shift and the resulting nitrogen geometry

Abstract: A set of azadiphosphiridine complexes 3a and 4b,c were synthesized in high selectivity using N-H and P-H deprotonation as key steps and RPCl2 as substrates (R = NiPr2 (a), -tBu...

Cited by 2 publications

References 24 publications

Ring Strain Energy of Diheteropnictogeniranes El2Pn (Pn=N, P, As, Sb)– Accurate versus Additive Approaches

Ring Strain Energy of Diheteropnictogeniranes El2Pn (Pn=N, P, As, Sb)– Accurate versus Additive Approaches

Synthesis of Pincer type carbene and their Ag(I)-NHC complexes, and their Antimicrobial activities

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Ring Strain Energy of Diheteropnictogeniranes El₂Pn (Pn=N, P, As, Sb)– Accurate versus Additive Approaches

Ring Strain Energy of Diheteropnictogeniranes El₂Pn (Pn=N, P, As, Sb)– Accurate versus Additive Approaches