TY  - JOUR
A1  - Rivera, Augusto
A1  - Uribe, Juan Manuel
A1  - Ríos-Motta, Jaime
A1  - Bolte, Michael
T1  - 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
T2  - Crystals
N2  - 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.
KW  - 3,30′-ethane-1,2-diyl-bis-1,3,5-triazabicyclo[3.2.1]octane
KW  - crystal structure
KW  - hyperconjugative interaction
KW  - aminal structure
KW  - NBO analysis
KW  - Bolhmann bands
Y1  - 2018
UR  - http://publikationen.ub.uni-frankfurt.de/frontdoor/index/index/docId/53573
UR  - https://nbn-resolving.org/urn:nbn:de:hebis:30:3-535730
SN  - 2073-4352
N1  - 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
VL  - 8
IS  - 6, Art. 251
SP  - 1
EP  - 14
PB  - MDPI
CY  - Basel
ER  -