Synthesis and structural studies of N‐(p‐toluenesulfonyl)‐amino acid 3,5‐di‐tert‐butyl‐2‐phenolamides

Tlahuextl, Margarita; Aguilar-Castro, Liliana; Camacho‐Camacho, Carlos; Contreras, Rosalinda

doi:10.1002/hc.10223

Cited by 3 publications

(9 citation statements)

References 14 publications

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“…However, it is the Z,Z conformer (B in Scheme 1) that is required to produce the cyclization reaction and the presence of these intramolecular hydrogen interactions avoids benzoxazole formation. We have found that tert-butyl groups in the benzene ring restrict the presence of intramolecular C6-H6•••O2 hydrogen-bonds 13 . The amide group in these compounds is not coplanar with the aromatic ring and electronic conjugation between these groups is unlikely.…”

Section: Bond X-h•••y Is An Interaction Wherein a Hydrogen Atom (Whmentioning

confidence: 93%

“…The molecular structure of these compounds is interesting because there are intramolecular O•••H•••N and C-H•••O interactions that constrain the geometry of the amide in the E,Z conformation (A in Scheme 1) 13 . However, it is the Z,Z conformer (B in Scheme 1) that is required to produce the cyclization reaction and the presence of these intramolecular hydrogen interactions avoids benzoxazole formation.…”

Section: Bond X-h•••y Is An Interaction Wherein a Hydrogen Atom (Whmentioning

confidence: 99%

“…The amide group in these compounds is not coplanar with the aromatic ring and electronic conjugation between these groups is unlikely. Thus, the presence of electron donor groups in the benzene ring restrict the participation of N-H in hydrogen-bond interactions and thus the Z,Z conformation (B in Scheme 1) is favored in these amides 13 . In order to analyze the electronic factors involved during the processes mentioned above, in this paper we synthesized six substituted N-(2-hydroxyphenyl)-2-[(4-methybenzenelsulfonyl)amino]acetamides 7-12 (Scheme 2).…”

Section: Bond X-h•••y Is An Interaction Wherein a Hydrogen Atom (Whmentioning

confidence: 99%

“…were obtained in yields above 75% by a established protocol [12][13] . The molecular structure of amides 7-12 was unequivocally established by FAB mass spectrometry, IR and NMR ( 1 H, 13 C, 15 N) spectroscopy.…”

Section: N-(2-hydroxyphenyl)-2-[(4-methylbenzenesulfonyl)amino]acetammentioning

confidence: 99%

“…The molecular structure of amides 7-12 was unequivocally established by FAB mass spectrometry, IR and NMR ( 1 H, 13 C, 15 N) spectroscopy.…”

Section: N-(2-hydroxyphenyl)-2-[(4-methylbenzenesulfonyl)amino]acetammentioning

confidence: 99%

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Hydrogen bond studies in substituted N-(2-hydroxyphenyl)-2-[(4-methylbenzenesulfonyl)amino]acetamides

Aguilar-Castro¹,

Tlahuextl²,

Mendoza-Huízar³

et al. 2007

Arkivoc

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Six substituted N-(2-hydroxyphenyl)-2- [(4-methylbenzensulfonyl)amino]acetamides 7-12 have been synthesized from 2-amino-3-nitrophenol, 2-amino-4-nitrophenol, 2-amino-5-nitrophenol, 2-amino-4-chlorophenol, 2-amino-4-tert-butylphenol, 2-amino-4-chloro-5-nitrophenol, and the [(4-methylbenzenesulfonyl) experiments on compounds 7-12 gave evidence for the formation of intra-and intermolecular hydrogen-bonds in solution. The molecular structure of 7 and 12 was determined by X-ray crystallography. The electronic behavior of the intramolecular hydrogen-bonds in these compounds was established by NBO studies.

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Section: Bond X-h•••y Is An Interaction Wherein a Hydrogen Atom (Whmentioning

confidence: 93%

Section: Bond X-h•••y Is An Interaction Wherein a Hydrogen Atom (Whmentioning

confidence: 99%

Section: Bond X-h•••y Is An Interaction Wherein a Hydrogen Atom (Whmentioning

confidence: 99%

Section: N-(2-hydroxyphenyl)-2-[(4-methylbenzenesulfonyl)amino]acetammentioning

confidence: 99%

“…The molecular structure of amides 7-12 was unequivocally established by FAB mass spectrometry, IR and NMR ( 1 H, 13 C, 15 N) spectroscopy.…”

Section: N-(2-hydroxyphenyl)-2-[(4-methylbenzenesulfonyl)amino]acetammentioning

confidence: 99%

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Hydrogen bond studies in substituted N-(2-hydroxyphenyl)-2-[(4-methylbenzenesulfonyl)amino]acetamides

Aguilar-Castro¹,

Tlahuextl²,

Mendoza-Huízar³

et al. 2007

Arkivoc

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Structural studies of spiroarsoranes derived from 2-aminophenols

et al. 2006

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This paper describes the structural studies of 2-phenyl-9,9 -dimethyl-2,2 -spirobis(1,3,2-λ 5 -benzoxazarsoline) 5, 2-phenyl-8,8 -dimethyl-2,2 -spirobis(1,3,2-λ 5 -benzoxazarsoline) 6 by 1 H, 13 C, 15 N NMR in [ 2 H 6 ]DMSO and CDCl 3 . The solid state studies were made by X-ray experiments. Infrared spectroscopy was obtained in CDCl 3 and the vibrational signals were assigned using DFT calculations. The nature of the As-N, As-C and As-O bonds in these compounds was established by NBO studies.

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15N NMR Spectroscopy in Structural Analysis: An Update (2001 - 2005)

Marek¹,

Lyčka²,

Kolehmainen³

et al. 2007

COC

134

110

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Since our previous review article (Curr. Org. Chem. 2002, 6, 35), significant improvements and an array of 15 N NMR applications in structural analysis have been published. This report aims to update coverage of improvements in methodology and various types of applications published over the period 2001 -2005. Substantial progress in cryogenic probe technology and the commercial availability of cryoprobes have facilitated the measurement of 15 N NMR parameters.The number of solid-state applications has increased significantly during the past few years. In contrast to our previous review, this article covers 15 N solid-state studies. The 15 N NMR chemical shifts of organic molecules are routinely measured by using cross-polarization magic-angle spinning (CP/MAS) techniques. The principal values of the chemical shift tensors can also be determined. 1 H-15 N and 2 H-15 N distance measurements made by means of 1 H detection are currently used in NMR crystallography.User friendly quantum chemical programs allow for the routine calculation of 15 N chemical shielding and indirect spinspin coupling constants, especially using density functional theory (DFT).Applications of 15 N NMR spectroscopy in various fields of chemistry are summarized here. Major sections represent tautomerism, complexation, protonation, and hydrogen bonding. The other topics comprise N-alkylation, N-oxidation, regioisomerism, and changes in configuration or conformation.

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Synthesis and structural studies of N‐(p‐toluenesulfonyl)‐amino acid 3,5‐di‐tert‐butyl‐2‐phenolamides

Cited by 3 publications

References 14 publications

Hydrogen bond studies in substituted N-(2-hydroxyphenyl)-2-[(4-methylbenzenesulfonyl)amino]acetamides

Hydrogen bond studies in substituted N-(2-hydroxyphenyl)-2-[(4-methylbenzenesulfonyl)amino]acetamides

Structural studies of spiroarsoranes derived from 2-aminophenols

15N NMR Spectroscopy in Structural Analysis: An Update (2001 - 2005)

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