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The 1H- and 2H-1,2,3-triazoles are isomeric five-membered ring, aromatic heterocycles that may undergo chemical equilibration by virtue of intramolecular hydrogen migration (tautomerization). Using millimeter-wave spectroscopy in the 130–375 GHz frequency range, we measured the spectroscopic constants for thirteen 1H-1,2,3-triazole and sixteen 2H-1,2,3-triazole isotopologues. Herein, we provide highly accurate and highly precise semi-experimental equilibrium (reSE) structures for the two tautomers based on the spectroscopic constants of each set of isotopologues, together with vibration–rotation interaction and electron-mass distribution corrections calculated using coupled-cluster singles, doubles, and perturbative triples calculations [CCSD(T)/cc-pCVTZ]. The resultant structures are compared with a “best theoretical estimate” (BTE), which has recently been shown to be in exceptional agreement with the semi-experimental equilibrium structures of other aromatic molecules. Bond distances of the 1H tautomer are determined to <0.0008 Å and bond angles to <0.2°. For the 2H tautomer, bond angles are also determined to <0.2°, but bond distances are less precise (2σ ≤ 0.0015). Agreement between BTE and reSE values is discussed.
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Synthesis of 2,5-Dibutyl-3,6-dimethyl-1 H ,2 H ,4 H ,5 H -pyrrolo[3,4- c ]pyrrole-1,4-dione: A Diketopyrrolopyrrole Scaffold for the Formation of Alkenyldiketopyrrolopyrrole Compounds
- Award ID(s):
- 1700982
- PAR ID:
- 10093213
- Date Published:
- Journal Name:
- Organic Letters
- Volume:
- 21
- Issue:
- 7
- ISSN:
- 1523-7060
- Page Range / eLocation ID:
- 1973 to 1978
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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2-R-1 H -1,3-Benzazaphospholes (R-BAPs) are an interesting class of σ 2 P heterocycles containing PC bonds. While closely related 2-R-1,3-benzoxaphospholes (R-BOPs) have been shown to be highly photoluminescent materials depending on specific R substituents, photoluminescence of R-BAPs has been previously limited to an example having a fused carbazole ring system. Here we detail the synthesis and structural characterization of a new R-BAP (3c, R = 2,2′-dithiophene), and compare its photoluminescence against two previously reported R-BAPs (3a, R, R′ = Me and 3b, R = 2-thiophene). The significant fluorescence displayed by the thiophene derivatives 3b ( φ = 0.53) and 3c ( φ = 0.12) stands in contrast to the weakly emissive methyl substituted analogue 3a ( φ = 0.08). Comparative computational investigations of 3a–c offer insights into the interplay between structure–function relationships affecting excited state relaxation processes.more » « less
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- Free Publicly Accessible Full Text
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Accepted Manuscript1.0
- Journal Article:
- https://doi.org/10.1021/acs.orglett.9b00019
