In an urban environment, radio-wave interaction with buildings may affect considerably the propagation of radio waves, mainly because of multipath, diffraction, and shadowing effects. This paper outlines the effect of two-dimensional (2-D) (vertical and lateral) diffraction and compares a Fresnel-Kirchhoff scalar approach to a vectorial geometrical theory of diffraction (GTD) approach applied to a four-ray system. The former can be considered as a generalization of conventional knife-edge diffraction theory while the latter (GTD) is useful in the context of ray tracing. A very good agreement between the Fresnel-Kirchhoff and GTD results is found within the limits of validity of both methods. Moreover, it is shown that conventional knife-edge diffraction theory can largely overestimate attenuation (10-15 dB) behind tall buildings in the center of a city environment. Different frequency bands have been tested for the sake of comparison, and emphasis has been put on the radio communications frequency bands used for the global system for mobile communications (GSM) and DCS/DECT systems at 900 and 1800 MHz.