The role of hyperconjugation on the structure and c–h stretching frequencies of 3,3′-ethane-1,2-diyl- bis-1,3,5-triazabicyclo[3.2.1]octane (etaboc): An x-ray structure and vibrational study

Structural and vibrational studies have been carried out for the most stable conformer of 3,3′-ethane-1,2-diyl-bis-1,3,5-triazabicyclo[3.2.1]octane (ETABOC) at the DFT/B3LYP/6-31G(dp) level using the Gaussian 03 software
Structural and vibrational studies have been carried out for the most stable conformer of 3,3′-ethane-1,2-diyl-bis-1,3,5-triazabicyclo[3.2.1]octane (ETABOC) at the DFT/B3LYP/6-31G(dp) level using the Gaussian 03 software. In light of the computed vibrational parameters, the observed IR Bolhmann bands for the C2V, C2, and Ci symmetrical structures of ETABOC have been analyzed. Hyperconjugative interaction was done by Natural Bond Orbital Analysis. Interpretation of hyperconjugative interaction involving the lone pairs on the bridgehead nitrogen atoms with the neighboring C–N and C–C bonds defines the conformational preference of the title compound. The recorded X-ray diffraction bond parameters were compared with theoretical values calculated at B3LYP/6-31G(d,p) and HF/6-31G(d,p) level of theory showed that ETABOC adopts a chair conformation and possesses an inversion center.
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Author:Augusto Rivera, Juan Manuel Uribe, Jaime Ríos-Motta, Michael Bolte
URN:urn:nbn:de:hebis:30:3-535730
DOI:http://dx.doi.org/10.3390/cryst8060251
ISSN:2073-4352
Parent Title (English):Crystals
Publisher:MDPI
Place of publication:Basel
Document Type:Article
Language:English
Date of Publication (online):2018/06/16
Date of first Publication:2018/06/16
Publishing Institution:Universitätsbibliothek Johann Christian Senckenberg
Release Date:2020/06/17
Tag:3,30′-ethane-1,2-diyl-bis-1,3,5-triazabicyclo[3.2.1]octane; Bolhmann bands; NBO analysis; aminal structure; crystal structure; hyperconjugative interaction
Volume:8
Issue:6, Art. 251
Pagenumber:14
First Page:1
Last Page:14
Note:
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited
HeBIS PPN:466838263
Institutes:Biochemie und Chemie
Dewey Decimal Classification:540 Chemie und zugeordnete Wissenschaften
Sammlungen:Universitätspublikationen
Licence (German):License LogoCreative Commons - Namensnennung 4.0

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