Ultraviolet spectrum of vinylamine

Pillsbury, Nathan R.; Drucker, Stephen

doi:10.1016/j.jms.2004.01.008

Cited by 6 publications

(3 citation statements)

References 24 publications

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“…Vinylamine is the simplest enamine and is thought to be a constituent of interstellar molecular clouds . Although it is a short-lived transient species, which is difficult to generate, it has been studied by microwave, , infrared, and ultraviolet spectroscopies. The structure was first determined by microwave spectroscopy, and the molecule was found to be nonplanar .…”

Section: Theoretical Sectionmentioning

confidence: 99%

“…The structure was first determined by microwave spectroscopy, and the molecule was found to be nonplanar . The nonplanarity was confirmed by a combined semirigid bender analysis of vibrational satellite shifts in the microwave spectrum and infrared data . The ab initio structure was also calculated in a number of investigations, but the highest level of calculation was MP2/6-311G**, which is not always sufficient to obtain an accurate geometry.…”

Section: Theoretical Sectionmentioning

confidence: 99%

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Microwave Spectrum, Structure, and Quantum Chemical Studies of a Compound of Potential Astrochemical and Astrobiological Interest: Z-3-Amino-2-propenenitrile

et al. 2006

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Z-3-Amino-2-propenenitrile, H2NCH=CHCN, a compound of astrochemical and astrobiological interest, has been studied by Stark and Fourier transform microwave spectroscopy along with eight of its isotopologues; the synthesis of five of these are reported. The spectra of the ground vibrational state and of three vibrationally excited states belonging to the two lowest normal modes were assigned for the parent species, whereas the ground states were assigned for the isotopologues. The frequency of the lowest in-plane bending fundamental vibration was determined to be 152(20) cm(-1) and the frequency of the lowest out-of-plane fundamental mode was found to be 176(20) cm(-1) by relative intensity measurements. A delicate problem is whether this compound is planar or slightly nonplanar. It was found that the rotational constants of the nine species cannot be used to conclude definitely whether the molecule is planar or not. The experimental dipole moment is mu(a) = 16.45(12), mu(b) = 2.86(6), mu(c) = 0 (assumed), and mu(tot.) = 16.70(12) x 10(-30) C m [5.01(4) D]. The quadrupole coupling constants of the two nitrogen nuclei are chi(aa) = -1.4917(21) and chi(cc) = 1.5644(24) MHz for the nitrogen atom of the cyano group and chi(aa) = 1.7262(18) and chi(cc) = -4.0591(17) MHz for the nitrogen atom of the amino group. Extensive quantum-chemical calculations have been performed, and the results obtained from these calculations have been compared with the experimental values. The equilibrium structures of vinylamine, vinyl cyanide, and Z-3-amino-2-propenenitrile have been calculated. These calculations have established that the equilibrium structure of the title compound is definitely nonplanar. However, the MP2/VQZ energy difference between the planar and nonplanar forms is small, only -423 J/mol. Z-Amino-2-propenenitrile and E-3-amino-2-propenenitrile are formed simply by mixing ammonia and cyanoacetylene at room temperature. A plausible reaction path has been modeled. G3 calculations indicate that the enthalpy (298.15 K, 1 atm) of the transition state is about 130 kJ/mol higher than the sum of the enthalpies of the reactants ammonia and cyanoacetylene. This energy difference is comparatively high, which indicates that both E- and Z-3-aminopropenenitrile are not likely to be formed in the gas phase in cold interstellar clouds via a collision between ammonia and cyanoacetylene. An alternative reaction between protonated cyanoacetylene (H-C[triple bond]C-C[triple bond]NH+) and ammonia is predicted to have a much lower activation energy than the reaction between the neutral molecules. Although protonated E- and Z-3-aminopropenenitrile in principle may be formed this way, it is more likely that a collision between NH3 and H-C[triple bond]C-C[triple bond]NH+ leads to NH4+ and H-C[triple bond]C-C[triple bond]N.

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Section: Theoretical Sectionmentioning

confidence: 99%

Section: Theoretical Sectionmentioning

confidence: 99%

Microwave Spectrum, Structure, and Quantum Chemical Studies of a Compound of Potential Astrochemical and Astrobiological Interest: Z-3-Amino-2-propenenitrile

et al. 2006

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“…Nonetheless, vinylamine was prepared by gas-phase pyrolysis via aliphatic amines, and the half-life of this molecule was about 10 min [15,16]. Additional work performed by Pillsbury and Drucker [17] reported that vinylamine is poorly stable at room temperature, exhibiting a half-life between 2-20 min. Our XPS data are inconsistent with regard to the stability of vinylamine, and hence, we confirm the existence of enamine tautomeric forms.…”

Section: Physicochemical Properties Of the Acmentioning

confidence: 99%

Polycondensation of Hexamethylenetetramine in Anhydrous Acid Media as a New Approach to Carbyne-Like Materials and Its Application as Dispersant of Carbon Materials

Gerasimova

Alekhina

García‐Cruz

et al. 2019

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Aminocumulene (AC), a technical name that results from the hexamethylenetetramine polycondensation in anhydrous sulfuric acid, was successfully performed toward the synthesis of oligomeric cumulenic compounds made up of carbyne-like (=C=C)x fragments as a main moiety together with amino endcapping groups. The tentative mechanism for the synthesis of the soluble and insoluble AC likely included the participation of carbene species as an intermediate. Spectral properties obtained from UV-Vis, infrared, and Raman spectroscopies, and surface chemistry analysis through X-ray photoelectron spectroscopy of the soluble AC confirmed the presence of a mixture of linear and branched aminocumulene-based oligomers. AC displayed high performance as a dispersant and stabilizer agent of both multi-walled carbon nanotubes and graphene in aqueous solutions after powerful insonation treatment under controlled temperature compared to the most commonly used dispersant agents. Thereby, AC is vitally important for the preparation of carbonaceous materials based on nanoinks in a wide variety of fields.

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Substituent effects on the nonadiabatic dynamics of ethylene: π-donors and π-acceptors

MacDonell

Schuurman

2018

Chemical Physics

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Ultraviolet spectrum of vinylamine

Cited by 6 publications

References 24 publications

Microwave Spectrum, Structure, and Quantum Chemical Studies of a Compound of Potential Astrochemical and Astrobiological Interest: Z-3-Amino-2-propenenitrile

Microwave Spectrum, Structure, and Quantum Chemical Studies of a Compound of Potential Astrochemical and Astrobiological Interest: Z-3-Amino-2-propenenitrile

Polycondensation of Hexamethylenetetramine in Anhydrous Acid Media as a New Approach to Carbyne-Like Materials and Its Application as Dispersant of Carbon Materials

Substituent effects on the nonadiabatic dynamics of ethylene: π-donors and π-acceptors

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