Dynamic respreading and maximum surface pressures are analyzed as a function of chain-backbone linkage, phosphate-phosphonate group, and N-headgroup structure for surface-excess films of dipalmitoyl phosphatidylcholine (DPPC), dipalmitoyl phosphatidylethanolamine (DPPE), and 13 related phospholipid and phosphonolipid analogs. Film behavior varied significantly with molecular structure, related in part to differences in molecular packing and mobility from ether vs amide vs ester linkages, as well as structure-induced variations in headgroup charge, hydration, hydrophobicity, hydrogen bonding, and steric bulk. Analysis of surface pressure-area isotherms from Wilhelmy balance experiments at three different pH values (H. Liu et at, J. Colloid Interface Sci. 167, 378-390) showed that : (1) diether phosphonolipid (DEPN) analog compounds had better respreading on successive cycles into the collapse regime compared to ether-amide phosphonolipid (EAPN) analogs with equivalent N-headgroups at pH 2.6, 5.6, and 11.5; (2) diether phospholipids (DHPC and DHPE) also had better respreading than corresponding diester phospholipids (DPPC and DPPE) at all three pH values; (3) the headgroup phosphonate vs phosphate linkage led to decreased cycle 2/cycle 1 respreading at all pH in the ethanolamine diether phosphonolipid DEPN-13 vs DHPE and in the choline diether phosphonolipid DEPN-8 vs DHPC, although cycle 7/cycle I respreading was improved in DEPN-8; (4) maximum surface pressures generated by PC-related compounds (DPPC, DHPC, DEPN-8, EAPN-9) were >70 mN/m independent of pH, while maximum pressures for PE-related compounds (DPPE, DHPE, DEPN-13, EAPN-13) were lower at 51-67 mN/m and varied more with pH; (5) respreading and maximum surface pressures did not vary in a consistent pattern as a function of pH for DEPN and EAPN analogs with different degrees of N-methylation, particularly at pH 11.5 where DEPN-10 and EAPN-10 with two N-methyl groups paradoxically had the lowest maximum surface pressures and best respreading of any compounds studied; and (6) the N-substitution of two hydroxyethyl groups for two methyl groups had less effect on surface behavior than N-substitution of methyl groups for hydrogen. The significant differences in dynamic respreading and maximum surface pressure found here for relatively small changes in molecular structure and headgroup charge indicate that specific compositional requirements likely exist for glycerophospholipids in functional pulmonary surfactant. The results also support the feasibility of synthesizing phospholipid-like molecules with specific surface-active properties for potential use in new exogenous lung surfactant mixtures.