<i>N</i>-[4-(Prop-2-ynyloxy)phenyl]maleimide

Li, Zhanxian; Ren, Cai-Mei; Yang, Sen; Yao, Guang-Jun; Shi, Qiu-Zhi

doi:10.1107/s1600536808035885

Cited by 2 publications

(1 citation statement)

References 7 publications

(7 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The title compound is an aryl propargyl ether derivative which attracts interest with regard to Claisen rearrangement (Kenny et al 2006;Wang et al 2012) or cleavage of the O-CH 2 bond by boron reagents (Yao et al 2009). For related structures of 4-(prop-2-yn-1-yloxy)benzenes, see: Lindeman et al (1993); Zhu et al (2006); Zhang et al (2008); Marsh (2009); Ranjith et al (2010); Li et al (2009); Ao et al Table 1 Hydrogen-bond geometry (Å , ).…”

Section: Related Literaturementioning

confidence: 99%

Crystal structure of 4-(prop-2-yn-1-yloxy)benzonitrile

Kanagawa

Okuno

2015

Acta Cryst E

View full text Add to dashboard Cite

In the title compound, C10H7NO, the dihedral angle between the aromatic ring and the prop-2-yn-1-yloxy grouping is 9.47 (10)°. The bond lengths indicate electronic conjugation between the cyano group, the benzene ring and the propynyloxy oxygen atom. In the crystal, a hydrogen bond between the acetylenic C—H atom and the cyano nitrogen atom link the molecules into wave-like [30-1] C(11) chains. These chains are connected by Csp 2—H⋯πac (πac is the acetylinic C—C triple bond) close contacts [2.794 (1) Å], resulting in a rolling sheet structure parallel to the ac plane and aromatic π–π stacking interactions between the sheets [centroid–centroid distance = 3.593 (2) Å] generate a three-dimensional network.

show abstract