Ethyl<i>N</i>-phenyloxamate

Garcı́a-Báez, Efrén V.; Gómez-Castro, Carlos Z.; Höpfl, Herbert; Martínez‐Martínez, Francisco J.; Padilla‐Martínez, Itzia I.

doi:10.1107/s0108270103017554

Cited by 9 publications

(7 citation statements)

References 10 publications

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“…The outof-plane conformation is characteristic of disubstituted ethyl o-and p-phenyl-bis-oxalamates, 13 in contrast with the reported planar conformation of monosubstituted ethyl N-phenyl oxalamate. 14…”

Section: Resultsmentioning

confidence: 99%

“…Furthermore, C-C (methyl) distances in the tert-butyl group were restrained to be the same for both orientations. The occupancies of the two sites converged at 0.646 (14) and 0.354 (14). Crystals suitable for X-ray analysis were obtained from THF (compounds 3 and 4), DMSO (compounds 5, 6 and 7) or N,N-dimethylformamide (compound 2).…”

Section: General Methodsmentioning

confidence: 99%

“…The resulting ring motif R 2 2 (16) is developed into 1-D columns by self-complementary amide N7-H7/O18 i hydrogen bonding interactions, which describe a second R 2 2 (16) ring motif. In addition, two p-interactions strengthen the column assembly: N7-H7/p i and pd-p-stacking i , this last with 4.5383(14) and ) developing along the direction of the a axis,Fig. 5.…”

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confidence: 99%

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Supramolecular architectures of conformationally controlled 1,3-phenyl-dioxalamic molecular clefts through hydrogen bonding and steric restraints

et al. 2011

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In this contribution the supramolecular architecture of a series of six 1,3-phenyl-dioxalamic molecular clefts is described. The conformation was controlled by the use of Me and OMe group substitution in the phenyl spacer. The structural and conformational study was carried out by X-ray diffraction analysis, DFT calculations at PBEPBE 6-31+G (3df, 3pd) theory level and variable temperature 1 H NMR in solution. The C2-Me group exerts a dual influence on the conformation adopting the endo(sc) or exo(ac) conformations in the oxalamic arms, meanwhile the C2-OMe group leads to the adoption of the exo(ap) conformation. DFT study results showed that the exo(ap)-exo(ap) conformation is more stable than the other conformations due to the conjugation that stabilizes the molecule and minimizes the conformational energy. Supramolecular arrays in oxalamate/oxalamide derivatives of 1,3diaminobenzene, 2-methyl-benzene-1,3-diamine and 2,4,6-trimethyl-benzene-1,3-diamine are directed by self-complementary N-H/O hydrogen bonding interactions, whose organization in the crystal depends on the twist of the oxalamic arms, meanwhile in oxalamate/oxalamide derivatives of 5-tertbutyl-2,6-diamineanisol with an exo(ap)-exo(ap) conformation, the supramolecular arrays are directed by p-stacking, dipolar carbonyl-carbonyl interactions and C-H/O soft contacts. N 1 ,N 10-(1,3-(2,4,6-Trimethyl)-phenyl)-bis-(N 2-(2-(2-hydroxyethoxy)ethyl)oxalamide) adopts the form of a supramolecular meso-helix, which is the first example of helical 1,3-phenyl-dioxalamide.

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Section: Resultsmentioning

confidence: 99%

Section: General Methodsmentioning

confidence: 99%

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confidence: 99%

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Supramolecular architectures of conformationally controlled 1,3-phenyl-dioxalamic molecular clefts through hydrogen bonding and steric restraints

et al. 2011

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“…S1 in ESI †). In addition, the natural charge distribution 32 showed that the terminal carboxyl group carries a negative charge (À0.804 e), whose absolute value is only slightly smaller than that calculated for Oxam at the same level of theory (À0.840 e), thus suggesting that the possibility to interact with the calcite surface through the carboxyl group 19 is preserved.…”

Section: Theoretical Calculationsmentioning

confidence: 78%

Oxamate salts as novel agents for the restoration of marble and limestone substrates: case study of ammonium N-phenyloxamate

et al. 2016

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The ammonium salt of N-phenyloxamic acid (AmPhOxam) was synthesised, characterised by FT-IR, FT-Raman, UV-Vis, 1H-NMR spectroscopic methods and single crystal X-ray diffraction, and evaluated as protective and consolidating agent for calcareous stone substrates under mild conditions. Hydroalcoholic solutions of AmPhOxam were tested for the treatment of naturally weathered white Marble and biomicritic limestone. Mercury intrusion porosimetry, FT-NIR spectroscopy measurements and SEM microscopy showed the formation of a superficial protective layer of crystals of the corresponding monohydrated calcium salt, CaPhOxam, on both treated stones

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“…Furthermore, the C1Á Á ÁO5 distance of 2.849 (3) Å (C1-H1AÁ Á ÁO5 = 102 ) suggests the formation of a weak intermolecular hydrogen-bonding interaction C1-H1AÁ Á ÁO5 (Desiraju, 1996), while the primary hard interaction N4-H4Á Á ÁO6 [N4Á Á ÁO6 = 2.703 (3) Å and N4-H4Á Á ÁO6 = 109 (2) ] completes the intramolecular hydrogenbonding scheme as an S(5)S(5) motif (Bernstein et al, 1995) ( Fig. 1), which is characteristic of oxalamates and oxamides derived from primary amines (Nuñ ez et al, 1988;García-Bá ez et al, 2003;Padilla-Martínez et al, 2003). Hydrogen-bonding geometries are listed in Table 2.…”

Section: Commentmentioning

confidence: 99%