Chromatography Forum

how can one determine whether a given analyte is acidic or basic if its not reported in literature.

If you are going by the Bronstead-Lowry definition of acids and bases, then you can look at the structure and see if there are any functional groups that would act as proton donors (acids) or proton acceptors (bases). If you are going by the Lewis definition, then you are looking for electron pair donors (bases) or electron pair acceptors (acids). (For example, boric acid is a Lewis acid but not a Bronstead acid). Some compounds will have both types of groups, and could act as either acids or bases.

If you don't know the structure, then you can dissolve it in water and measure the pH.

It is very difficult to give a right answer here if you meant the determination of acidity/basicity from the structure (theoretically not experimentally, the latter can be relatively simple as MG indicated). Thus if one thinks of boric acid as B(OH)3 one could well guess that it may donate a H+ (Broenstedt...) in anology to H2SO4. Boron trifluoride (BF3) might have been a better example of a Lewis acid (if you bend Arrhenius and B-L a bit it also fits, though), what´s a good example of a Lewis base? Ether?
The Arrhenius definition (acid: any substance delivering H+ to the solution; base: any substance delivering OH- to the soluton) and the Broenstedt-Lowry are more empirical, the Lewis more theoretical in nature, the latter is, therefore, more useful in predicting from structure, especially if you know about the octed rule.

my analyte is insoluble in water.

its IUPAC name is

3- Ethyl-2,5 dihydro-4-methyl-N-[2-[4-[[[(trans-4-methylcyclohexyl)-amino]carbonyl]amino]sulfonyl]phenyl]ethyl]2-oxo-1H-pyrrole-1-carboxamide.