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Four related diethyl [(arylamino)(4‐ethynylphenyl)methyl]phosphonates

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Crystal structures are reported for four related diethyl [(arylamino)(4‐ethynylphenyl)lmethyl]phosphonate derivatives, namely diethyl [(4‐bromoanilino)(4‐ethynylphenyl)methyl]phosphonate, C19H21BrNO3P, (I), diethyl ((4‐chloro‐2‐methylanilino){4‐[2‐(trimethylsilyl)ethynyl]phenyl}methyl)phosphonate, C23H31ClNO3PSi, (II), diethyl ((4‐fluoroanilino){4‐[2‐(trimethylsilyl)ethynyl]phenyl}methyl)phosphonate, C22H29FNO3PSi, (III), and diethyl [(4‐ethynylphenyl)(naphthalen‐2‐ylamino)methyl]phosphonate, C23H24NO3P, (IV). The conformation of the anilinobenzyl group is very similar in all four compounds. The P—C bond has an approximately staggered conformation, with the aniline and ethynylphenyl groups in gauche positions with respect to the P=O double bond. The two six‐membered rings are almost perpendicular. The sums of the valence angles about the N atoms vary from 344 (2) to 351 (2)°. In the crystal structures, molecules of (I), (III) and (IV) are arranged as centrosymmetric or pseudocentrosymmetric dimers connected by two N—H...O=P hydrogen bonds. The molecules of (II) are arranged as centrosymmetric dimers connected by Cmethyl—H...O=P hydrogen bonds. The N—H bond of (II) is not involved in hydrogen bonding.
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Document Type: Research Article

Publication date: October 15, 2013

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