Conformational Properties of cis- and trans-N-Cyclopropylformamide Studied by Microwave Spectroscopy and Quantum Chemical Calculations was written by Samdal, Svein;Moellendal, Harald;Guillemin, Jean-Claude. And the article was included in Journal of Physical Chemistry A in 2015.Safety of N-Cyclopropylformamide This article mentions the following:
The microwave spectra of cis- and trans-N-cyclopropylformamide, C3H5NHC(=O)H, were studied in the 31-123 GHz spectral region at room temperature Rotational isomerism about the Cring-N bond is possible for both cis and trans. MP2/cc-pVTZ and CCSD/cc-pVTZ calculations indicate that there are two conformers in the case of cis, called Cis I and Cis II, while only one rotamer, denoted Trans, exists for trans-N-cyclopropylformamide. The quantum chem. methods predict that Cis I has an electronic energy that is 8-9 kJ/mol higher than the energy of Cis II. The CCSD H-Cring-N-H dihedral angle is 0.0° in Cis I, 93.0° in Cis II and 79.9° in Trans. The CCSD and MP2 calculations predict a slightly nonplanar structure for the amide moiety in both Trans and Cis II, whereas Cis I is computed to have a planar amide group bisecting the cyclopropyl ring. Surprisingly, the MP2 and CCSD methods predict practically the same energy for Trans and Cis II. The spectra of Cis II in the ground state and in two vibrationally excited states were assigned, while the spectrum of Cis I was not found presumably because of a low Boltzmann population due to a relatively large energy difference (8-9 kJ/mol). The spectra of the ground vibrational state and seven vibrationally excited states of Trans, were assigned. Vibrational frequencies of several of the excited state of both Cis II and Trans were determined by relative intensity measurements. The exptl. and CCSD rotational constants are in satisfactory agreement. The MP2 values of the quartic centrifugal distortion constants of both species are in relatively poor agreement with their exptl. counterparts. The MP2 vibration-rotation constants and sextic centrifugal distortion constants have little resemblance with the corresponding exptl. values. In the experiment, the researchers used many compounds, for example, N-Cyclopropylformamide (cas: 58644-54-5Safety of N-Cyclopropylformamide).
N-Cyclopropylformamide (cas: 58644-54-5) belongs to amides. In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well. Thus amides can participate in hydrogen bonding with water and other protic solvents; the oxygen atom can accept hydrogen bonds from water and the N–H hydrogen atoms can donate H-bonds. Amides can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.Safety of N-Cyclopropylformamide
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics