5-Azido-2-methoxy-1,3-xylyl-18-crown-5 has been prepared by reacting p-toluenesulfonyl azide with the carbanion generated from the reaction of 5-bromo-2-methoxy-1,3-xylyl-18-crown-5 with n-butyl lithium. The asymmetric N 3 stretch of this product has been observed as a single band at 2110 cm -1 in dichloromethane solution. Addition of solid NaSCN, KSCN and CsSCN shifts this band to 2115, 2113 and 2112 cm -1 , respectively. Computational studies of this azide at the B3LYP-6-31G* level in the presence and absence of Na + predicted these bands to be at 2173 cm -1 and 2184 cm -1. For the salt-containing solutions, additional bands were observed at 2066 cm -1 , 2056 cm -1 and 2055 cm -1 , respectively, which are in the range expected for CN stretches. The X-ray structure of this azide has been determined. The terminal and internal N-N bond lengths were found to be 1.127(2) and 1.245(2) , respectively, which is the usual pattern for aromatic azides. The crown ether is looped over the face of the aromatic ring resulting in an angle of 38.94° between the plane defined by the aromatic ring and that defined by the five ring oxygen atoms. In addition, the CH 3 group is rotated out of the plane of the phenyl ring with C1-C18-O181-C182 and C17-C18-O181-C182 dihedral angles of 93.81(14)° and -90.54(14)°, respectively.
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