On May 2, 1996, at an undetermined time, an Aero Commander 500-B, N50GV, became missing, and is assumed destroyed, while over the Caribbean Sea. The airline transport pilot, and both passengers are missing, and presumed fatally injured. The airplane was being operated under the provision of Title 14 CFR Part 135 by Domtrav Airways of St. Croix, Virgin Islands. Visual meteorological conditions existed at the time, and a visual flight rules (VFR) flight plan had been filed for the flight. The flight departed St. Croix at about 0821, and was destined for Dominica. Company personnel stated that the missing airplane departed immediately after another company airplane (N95HM). They stated that both aircraft were flying the same route of flight to Dominica, but were landing at different airports on the island. The pilot of N95HM talked the pilot of the missing airplane about 5 minutes after departure. The pilot of the missing airplane informed the pilot of N95HM that the airplane was having generator problems, and that he would continue to monitor them. The pilot of N95HM canceled the VFR flight plans for both aircraft upon reaching the Guadeloupe Boundary at 0856. He continued to Melville Hall, Dominica, arriving at about 0935, and waited for N50GV. After waiting about 1 1/2 to 1 3/4 hours for N50GV to arrive, a telephone and ramp search was initiated with negative results. An aerial search was initiated by N95HM at 1500 with negative results. A search was initiated by the United States Coast Guard on May 3, 1996. All shipping vessels located along N50GV flight course in the Atlantic Ocean and the Caribbean Sea were requested to look for the overdue airplane, and to report any sightings. No sightings were reported. The search was terminated on May 4, 1996. Geostationary Operational Environmental Satellite Data was reviewed by the NTSB Meteorologist. The images indicate scattered clouds were present along the route from St. Croix, Virgin Islands, to Canfield Airport in Dominica. There was no significant convective activity. Review of continuous data recording (CDR) generated by San Juan Combined Enroute Radar Approach, revealed no discrete radar targets that could be attributed to N50GV.