PMID- 35478783
OWN - NLM
STAT- PubMed-not-MEDLINE
LR  - 20220716
IS  - 2046-2069 (Electronic)
IS  - 2046-2069 (Linking)
VI  - 11
IP  - 35
DP  - 2021 Jun 15
TI  - In acid-aminopyrimidine continuum: experimental and computational studies of 
      furan tetracarboxylate-2-aminopyrimidinium salt.
PG  - 21463-21474
LID - 10.1039/d1ra01714d [doi]
AB  - Salts and cocrystals are the two important solid forms when a carboxylic acid 
      crystallizes with an aminopyrimidine base such that the extent of proton transfer 
      distinguishes between them. The DeltapK (a) value (pK (a)(base) - pK (a)(acid)) 
      predicts whether the proton transfer will occur or not. However, the DeltapK (a) 
      range, 0 < DeltapK (a) < 3, is elusive where the formation of cocrystal or salt 
      cannot be predicted. The current study has been done to obtain a generalization 
      in this elusive range with the Cambridge Structural Database (CSD). Based on the 
      generalization, a novel salt (FTCA)(-)(2-AP)(+) of furantetracarboxylic acid 
      (FTCA) with 2-aminopyrimidine (2-AP) is obtained. The structural confirmation was 
      done by single-crystal X-ray diffraction (SCXRD). Density functional theory (DFT) 
      calculations were performed at the IEF-PCM-B3LYP-D3/6-311G(d,p) level to optimize 
      the geometrical coordinates of salt for frontier molecular orbitals (FMOs) and 
      molecular electrostatic potential (MESP). The geometrical parameters of most of 
      the atoms of the optimized salt structure were comparable with SCXRD data. 
      Additionally, results of other computational methods such as ab initio 
      (Hartree-Fock; HF and second-order-Moller-Plesset perturbation; MP2) and 
      semi-empirical were also compared with experimental results of the salt. Quantum 
      theory of atoms in molecules (QTAIM), reduced density gradient (RDG), and natural 
      bond orbital (NBO) analyses were done to calculate the strength and nature of 
      non-covalent interactions present in the salt. Furthermore, Hirshfeld surface 
      analysis, interaction energy calculations, and total energy frameworks were 
      performed for qualitative and quantitative estimations of strong and weak 
      intermolecular interactions.
CI  - This journal is (c) The Royal Society of Chemistry.
FAU - Garg, Utsav
AU  - Garg U
AUID- ORCID: 0000-0002-2294-0314
AD  - Department of Applied Chemistry, Zakir Husain College of Engineering & 
      Technology, Aligarh Muslim University Aligarh 202002 Uttar Pradesh India 
      yasser.azim@gmail.com.
FAU - Azim, Yasser
AU  - Azim Y
AUID- ORCID: 0000-0002-3978-9171
AD  - Department of Applied Chemistry, Zakir Husain College of Engineering & 
      Technology, Aligarh Muslim University Aligarh 202002 Uttar Pradesh India 
      yasser.azim@gmail.com.
FAU - Alam, Mahboob
AU  - Alam M
AD  - Division of Chemistry & Biotechnology, Dongguk University 123 Dongdae-ro Gyeongju 
      Republic of Korea mahboobchem@gmail.com.
LA  - eng
PT  - Journal Article
DEP - 20210617
PL  - England
TA  - RSC Adv
JT  - RSC advances
JID - 101581657
PMC - PMC9034213
COIS- There are no conflicts to declare.
EDAT- 2022/04/29 06:00
MHDA- 2022/04/29 06:01
PMCR- 2021/06/17
CRDT- 2022/04/28 06:12
PHST- 2021/03/04 00:00 [received]
PHST- 2021/06/08 00:00 [accepted]
PHST- 2022/04/28 06:12 [entrez]
PHST- 2022/04/29 06:00 [pubmed]
PHST- 2022/04/29 06:01 [medline]
PHST- 2021/06/17 00:00 [pmc-release]
AID - d1ra01714d [pii]
AID - 10.1039/d1ra01714d [doi]
PST - epublish
SO  - RSC Adv. 2021 Jun 17;11(35):21463-21474. doi: 10.1039/d1ra01714d. eCollection 
      2021 Jun 15.