Competition and cooperativity of hydrogen-bonding and tetrel-bonding interactions involving triethylene diamine (DABCO), H 2 O and CO 2 in air

• Published in: New journal of chemistry Vol. 44; no. 6; pp. 2328 - 2338
• Main Authors: Yang, Jianming, Yu, Qinwei, Yang, Fang-Ling, Lu, Ka, Yan, Chao-Xian, Dou, Wei, Yang, Lizi, Zhou, Pan-Pan
• Format: Journal Article
• Language: English
• Published: 10.02.2020
• ISSN: 1144-0546; 1369-9261
• DOI: 10.1039/C9NJ06036G

Triethylene diamine (DABCO) has the characteristic of being hydrophilic and exhibits a color change in air because its N atom can interact with H 2 O and CO 2 . To understand these phenomena, herein, theoretical calculations on the intermolecular interactions between DABCO and H 2 O (or CO 2 ) were carried out at the M06-2X/aug-cc-pVDZ level without and with the counterpoise method, and single-point calculations at the CCSD(T)/aug-cc-pVDZ level were also performed. The electron donating ability of DABCO was revealed by the molecular surface electrostatic potential and Fukui function. The driving forces for the formation of a dimer and trimer were uncovered by EDA analyses. Because DABCO can interact with both H 2 O and CO 2 , the formation of hydrogen bonds and tetrel bonds is competitive, and meanwhile, DABCO can interact with H 2 O and CO 2 simultaneously, so the hydrogen bond and tetrel bond can coexist and cooperate with each other. The hydrogen bond and tetrel bond in the dimers and trimers were proven and analyzed by NCI and QTAIM. The results presented here will provide useful insight in understanding the hydrophilic characteristic and the color change of DABCO.