4-Allyl-2-methoxy-5-nitrophenyl acetate

Carrasco-Altamirano, Hector; Espinoza-Catalán, Luis; Gallardo-Araya, Claudio; Villada, Wilson Cardona; Ibáñez, Andrés; Alvarez‐Thon, Luis

doi:10.1107/s1600536806012177

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“…A search of the Cambridge Structural Database (CSD, Version 5.40, May 2019; Groom et al, 2016) of eugenol derivatives revealed two compounds with very similar structures but with a different position of the nitro group or with the hydroxide group substituted by an acetate group, viz. 4-allyl-2methoxy-5-nitrophenyl acetate (refcode: TEJREG; Carrasco-Altamirano et al, 2006) and 4-hydroxy-3-methoxy-5-nitroacetophenone (5-nitroapocynin) (MUCDOE; Babu et al, 2009). A third related compound, 4-hydroxy-3-methoxy-5nitrobenzaldehyde, has recently been reported (Vusak et al, 2020).…”

Section: Database Surveymentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of 4-allyl-2-methoxy-6-nitrophenol

et al. 2020

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The asymmetric unit of the title compound, C10H11NO4, which was synthesized via nitration reaction of eugenol (4-allyl-2-methoxyphenol) with a mixture of nitric acid and sulfuric acid, consists of three independent molecules of similar geometry. Each molecule displays an intramolecular hydrogen bond involving the hydroxide and the nitro group forming an S(6) motif. The crystal cohesion is ensured by intermolecular C—H...O hydrogen bonds in addition to π–π stacking interactions between the aromatic rings [centroid–centroid distances = 3.6583 (17)–4.0624 (16) Å]. The Hirshfeld surface analysis and the two-dimensional fingerprint plots show that H...H (39.6%), O...H/H...O (37.7%), C...H/H...C (12.5%) and C...C (4%) are the most important contributors towards the crystal packing.

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Section: Database Surveymentioning

confidence: 99%