The answer to this question will depend of such:
1. What is the dicarboxylic acid. Is COOH groups in such position the 5, 6-member or may me 7- member rings with aminogoups of DETA is possible to built. Or only a poly salts or polyamides we can obtain.
2. What is the ratio of reagents. In different ratio different product as monomer or olygimeric stucture will appear
3. What is the temperature of reacton. May be we obtain salts only at mild conditions of we obtain amides at severe conditions
In a neutral medium is the most reactive central nitrogen atom (a secondary amine).
Further consultations on request, specifications of dicarboxylic acids or its functional derivative must be done.
pKa values ( for tri-protonated salt): 3.58, 8.86, 9.65 (pKb=14-pKa); nukleophilicity correlated with bazicity.
Sayed,
This type of reaction will first form ammonium salts (ionic bonds) then transfer to amide bonds (covalent bonds) leading to polymeric material. See
--- Riehle, Richard James U.S., 6429267, 06 Aug 2002
--- Hagiopol, Cornel et al U.S. Pat. Appl. Publ., 20140166223, 19 Jun 2014 [45 min, reflux; rt → 140°C; 140°C → 155°C]
--- Kubo, Shinji and Matsumoto, Koji Jpn. Kokai Tokkyo Koho, 2011256342, 22 Dec 2011 [ C:H2SO4, S:H2O, rt → 145°C; 1 h, 145°C; 18 h, 140-160°C]
*Literature survey showed that the terminal amino groups are the ones involved in the amide bond formation
Good luck
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