Density functional calculations coupled with quantum theory of atoms in molecules analysis were carried out on Group 4 and 6 metallatranes with special emphasis on the nature of transannular M center dot center dot center dot N bonds present in these molecules. Substituents at both the apical and equatorial positions are found to influence the extent of transannular interaction. The degree of pyramidalization around the metal and the bridgehead nitrogen atom play a key role in strengthening or weakening the M center dot center dot center dot N bond. The stability of these molecules are found to depend to a large extent on the strength of M center dot center dot center dot N bonds with significant contribution coming in from metal-equatorial and metal-apical bonds, Group 6 metallatranes are found to have stronger transannular bonds and, hence, higher stabilization energies than their Group 4 counterparts, Atoms in molecules theory analysis reveals the presence of a considerable amount of covalent character in the M center dot center dot center dot N bonds which increase from Group 4 to Group 6.