Synthesis and IR, UV, NMR (1H and 11B), and mass spectral studies of new .beta.-ketoamine complexes of boron: crystal an molecular structure of OC6H4OBOC(R)CHC(R')NR" (R = p-ClC6H4, R' = C6H5, R" = CH3)

Singh, Yash Pal; Rupani, P.; Singh, Anirudh; Audhesh, K.; Mehrotra, R. C.; Rogers, Robin D.; Atwood, Jerry L.

doi:10.1021/ic00237a030

Cited by 38 publications

(17 citation statements)

References 2 publications

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“…A band for ν C = N has appeared at 1610-1630 cm -1 in all these derivatives with a small shift (10~15 cm -1 ) towards lower wave numbers compared with its position in the free ligands. This indicates the coordination of nitrogen atom to boron, which is further supported by the appearance of a new band for ν B←N at 805-820 cm -1 (Singh et al, 1986). Disappearance of a weak broad enolic ν C-OH band (observed in the spectra of the ligands in the range of 2700-3000 cm -1 ) in the spectra of 2a-f derivatives revealed the deprotonation of the enolic OH.…”

Section: Spectroscopic Studies Ir Spectramentioning

confidence: 64%

Some heteroleptic boron derivatives and their isomers derived from Schiff bases and glycol: synthesis, characterization and antimicrobial activities

Jangir

Sharma

et al. 2016

Main Group Metal Chemistry

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Some new heteroleptic boron derivatives of the type OCH 2 C(CH 3 ) 2 CH 2 OBO(CH 3 )C:CHC(R):N(R′)OH [where R = CH 3 , R′ = (CH 2 ) 2 (2a); (CH 2 ) 3 (2b); CH(CH 3 )CH 2 (2c), R = C 6 H 5 , R′ = (CH 2 ) 2 (2d); (CH 2 ) 3 (2e); CH(CH 3 )CH 2 (2f)] have been synthesized by the reactions of tri-isopropyl borate with bifunctional tridentate Schiff bases and 2,2-dimethyl propane 1,3-diol in 1:1:1 molar ratio in refluxing benzene. Four isomers of corresponding heteroleptic derivatives 2a, 2b, 2e and 2f having the general formula OCH 2 C(CH 3 ) 2 CH 2 OBO(R′)N:C(R)CH:C(CH 3 )OH[where R = CH 3 , R′ = (CH 2 ) 2 (3a); (CH 2 ) 3 (3b), R = C 6 H 5 , R′ = (CH 2 ) 3 (3e); CH(CH 3 )CH 2 (3f) have also been synthesized by adopting different synthetic two-step processes. All these compounds have been characterized by elemental analyses, and their tentative structures have been proposed on the basis of IR, 1 H, 13 C, 11B NMR spectroscopic and FAB mass spectrometric studies. Schiff base ligands and their corresponding heteroleptic boron derivatives (2a-f) have also been screened for antimicrobial activities against pathogenic bacteria and fungi.

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Section: Spectroscopic Studies Ir Spectramentioning

confidence: 64%

Some heteroleptic boron derivatives and their isomers derived from Schiff bases and glycol: synthesis, characterization and antimicrobial activities

Jangir

Sharma

et al. 2016

Main Group Metal Chemistry

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“…C=O interaction. C=O bond lengthening during electrophilic addition of Lewis acids to carbonyl groups is also documented by calculation and experiment, with C-0 distances for C=O..;A (A = Lewis acid) systems ranging from 1.244 to 1.33 A (20,21,(33)(34)(35)(36)(37). Nucleophilic and electrophilic forces both play a fundamental role in the formation and stability of 6 and 3, adducts in which formaldehyde is trapped in a push-pull mechanism.…”

Section: Resultsmentioning

confidence: 80%

Structural studies of organoboron compounds. XXVIII. 5,5-Trimethylene-2,2-diphenyl-1,3-dioxa-5-azonia-2-boratacyclohexane and 5,5-dimethyl-2,2-diphenyl-1,3-dioxa-5-azonia-2-boratacyclohexane monohydrate

Kliegel¹,

Rettig²,

Trotter³

1988

Can. J. Chem.

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. 66, 377 (1988).The preparation of the title compounds demonstrates the bis-N-alkylation of secondary amines by formaldehyde, these labile ammonium inner salts being captured as diphenylboron chelates. Crystals of 5,5-trimethylene-2,2;diphenyl-l,3-dioxa-5-azonia-2-boratacyclohexane are orthorhombic, a = 8.8461(3), b = 10.7290(4), c = 15.8773(5) A, Z = 4, space group P212121, and those of 5,5-dimethyl-2,2-diphenyl-1,3-dioxa-5-azonia-2-boratacyclohexane monohydrate are monoclinic, a = 6.2432(3), b = 17.1469(8), c = 14.3701(5) A, P = 90.647(3)", Z = 4, space group P21/n. Both structures were solved by direct methods and were refined by full-matrix least-squares procedures to R = 0.030 and 0.047 for 1400 and 2258 reflections with I ? 3 u ( l ) , respectively. Both compounds have a B,N-betaine structure, the six-membered chelate rings adopting chair conformations. Libration-corrected bond lengths, 0-B = 1.508 (3) [Traduit par la revue] Introduction The alkylation of N,N-dialkylhydroxylamines 1 by formaldehyde leads to labile adducts 2 which can be trapped as diphenylboron chelates 3, as shown for N,N-dimethylhydroxylamine ( I , R = CH3) by an X-ray crystallographic analysis (I). The formal insertion of methylene into 1 results in N-hydroxymethylamines 4 which are also described as zwitterionic primary adducts of formaldehyde and an amine (2). Formaldehyde adducts of dialkylamine (3) are known as very labile compounds2 and exist generally as short-lived intermediates during the formation of enamines, aminals, iminium salts, Mannich bases, or similar compounds. Compared to the hydroxylamines 1, the hydroxymethylamines 4 should be nucleophilic enough to add a second molecule of formaldehyde in a reversible reaction to give the labile intermediate 5 by N-alkylation of the tertiary amine, or an intermediate 7 by 0-alkylation of the zwitterionic form. As reported in a preliminary communication (3), the dialkylamine-bisformaldehyde adducts can also be captured as diphenylboron chelates which are stable crystalline materials. A cyclic B,N-betaine structure

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“…Formation of B ← N dative bond is supported by the appearance of a new band for B ← N stretching vibration [23,24] at 810-820 cm −1 . Disappearance of a weak broad enolic νC-OH band [25,26] (observed in the spectra of the ligands in the range 2700-3000 cm −1 ) in the spectra of 1a-1e derivatives revealed the deprotonation of the enolic OH.…”

Section: Ir Spectramentioning

confidence: 92%

Syntheses, silylation, characterization, and antimicrobial and antifertility activities of organoboron derivatives of some bioactive monofunctional bidentate semicarbazones

Bhomia

Sharma

Lakhne

et al. 2017

Applied Organom Chemis

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Synthesis and IR, UV, NMR (1H and 11B), and mass spectral studies of new .beta.-ketoamine complexes of boron: crystal an molecular structure of OC6H4OBOC(R)CHC(R')NR" (R = p-ClC6H4, R' = C6H5, R" = CH3)

Cited by 38 publications

References 2 publications

Some heteroleptic boron derivatives and their isomers derived from Schiff bases and glycol: synthesis, characterization and antimicrobial activities

Some heteroleptic boron derivatives and their isomers derived from Schiff bases and glycol: synthesis, characterization and antimicrobial activities

Structural studies of organoboron compounds. XXVIII. 5,5-Trimethylene-2,2-diphenyl-1,3-dioxa-5-azonia-2-boratacyclohexane and 5,5-dimethyl-2,2-diphenyl-1,3-dioxa-5-azonia-2-boratacyclohexane monohydrate

Syntheses, silylation, characterization, and antimicrobial and antifertility activities of organoboron derivatives of some bioactive monofunctional bidentate semicarbazones

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