formaldehyde oxime

Formula: CH₃NO
Molecular weight: 45.0406
IUPAC Standard InChI: InChI=1S/CH3NO/c1-2-3/h3H,1H2
IUPAC Standard InChIKey: SQDFHQJTAWCFIB-UHFFFAOYSA-N
CAS Registry Number: 75-17-2
Chemical structure:
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Reaction thermochemistry data

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Data compiled by: John E. Bartmess

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Individual Reactions

CH₂NO^- + = formaldehyde oxime

By formula: CH₂NO^- + H⁺ = CH₃NO

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	<372.20	kcal/mol	Acid	DiDomenico and Franklin, 1972	gas phase; From MeNO2. G3MP2B3 calculations indicate a HOF(A-) of +3 kcal/mol

Gas phase ion energetics data

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Data evaluated as indicated in comments:
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to CH₃NO⁺ (ion structure unspecified)

Quantity	Value	Units	Method	Reference	Comment
IE (evaluated)	10.11	eV	N/A	N/A	L

Ionization energy determinations

IE (eV)	Method	Reference	Comment
10.11	PE	Dognon, Pouchan, et al., 1984	LBLHLM
10.1	PE	Frost, Lau, et al., 1982	LBLHLM
10.61	PE	Dognon, Pouchan, et al., 1984	Vertical value; LBLHLM
10.59 ± 0.02	PE	Frost, Lau, et al., 1982	Vertical value; LBLHLM
10.62	PE	Dargelos and Sandorfy, 1977	Vertical value; LLK

De-protonation reactions

CH₂NO^- + = formaldehyde oxime

By formula: CH₂NO^- + H⁺ = CH₃NO

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	<372.20	kcal/mol	Acid	DiDomenico and Franklin, 1972	gas phase; From MeNO2. G3MP2B3 calculations indicate a HOF(A-) of +3 kcal/mol; B

Vibrational and/or electronic energy levels

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Data compiled by: Marilyn E. Jacox

State: X

Vib. sym.	No.	Approximate type of mode	cm^-1		Med.	Method	References


a'	1	OH stretch	3650.29	vs	gas	IR	Califano and Luttke, 1956 Azman, Hadzi, et al., 1970 Duxbury, 1988
	2	CH₂ stretch	3109.72	w	gas	IR	Califano and Luttke, 1956 Azman, Hadzi, et al., 1970 Duxbury, 1988
	3	CH₂ stretch	2973.17	w m	gas	IR	Califano and Luttke, 1956 Azman, Hadzi, et al., 1970 Duxbury, 1988
	4	C=N stretch	1639.48	w m	gas	IR	Califano and Luttke, 1956 Azman, Hadzi, et al., 1970 Bannai and Duxbury, 1994
	5	CH₂ scissors	1410.48	m s	gas	IR	Califano and Luttke, 1956 Azman, Hadzi, et al., 1970 Bannai and Duxbury, 1994
	6	OH bend	1318.98	vs	gas	IR	Califano and Luttke, 1956 Azman, Hadzi, et al., 1970 Bannai and Duxbury, 1994
	7	CH₂ rock	1166	m	gas	IR	Califano and Luttke, 1956 Azman, Hadzi, et al., 1970
	8	NO stretch	892.58	s	gas	IR	Califano and Luttke, 1956 Azman, Hadzi, et al., 1970 Duxbury, Percival, et al., 1988 Bannai and Duxbury, 1994
	9	CNO deform.	530	w	gas	IR	Califano and Luttke, 1956 Azman, Hadzi, et al., 1970
a	10	CH₂ OPLA	952.61	s	gas	IR	Califano and Luttke, 1956 Azman, Hadzi, et al., 1970 Duxbury, Percival, et al., 1988
	11	CH₂ torsion	774.1	m	gas	IR	Califano and Luttke, 1956 Azman, Hadzi, et al., 1970 Duxbury, Percival, et al., 1988
	12	OH torsion	400	T	gas	IR	Califano and Luttke, 1956 Azman, Hadzi, et al., 1970

Additional references: Jacox, 1994, page 320; Jacox, 1998, page 314; Levine, 1962; Levine, 1963; Kaushik and Takagi, 1978; Klesing and Sutter, 1990

Notes

Weak

Medium

Strong

Very strong

Tentative assignment or approximate value

References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Vibrational and/or electronic energy levels, NIST Free Links, Notes

DiDomenico and Franklin, 1972
DiDomenico, A.; Franklin, J.L., Negative ions in the mass spectrum of nitromethane, Int. J. Mass Spectrom. Ion Phys., 1972, 9, 171. [all data]

Dognon, Pouchan, et al., 1984
Dognon, J.P.; Pouchan, C.; Dargelos, A.; Flament, J.P., Ab initio CI study and vibronic analysis of the photoelectron spectra of formaldoxime, Chem. Phys. Lett., 1984, 109, 492. [all data]

Frost, Lau, et al., 1982
Frost, D.C.; Lau, W.M.; McDowell, C.A.; Westwood, N.P.C., A study by He I photoelectron spectroscopy of monomeric nitrosomethane, the cis and trans dimers, and formaldoxime, J. Phys. Chem., 1982, 86, 3577. [all data]

Dargelos and Sandorfy, 1977
Dargelos, A.; Sandorfy, C., The photoelectron and far-ultraviolet absorption spectra of simple oximes, J. Chem. Phys., 1977, 67, 3011. [all data]

Califano and Luttke, 1956
Califano, S.; Luttke, W., Infrarotuntersuchungen an Oximen II., Z. Phys. Chem., 1956, 6, 1_2, 83, https://doi.org/10.1524/zpch.1956.6.1_2.083 . [all data]

Azman, Hadzi, et al., 1970
Azman, A.; Hadzi, D.; Kidric, J.; Orel, B.; Trampuz, C., Spectrochim. Acta, 1970, 27A, 2499. [all data]

Duxbury, 1988
Duxbury, G., High-resolution infrared spectrum of formaldoxime (CH2NOH) in the 3-μm and OH overtone regions, J. Mol. Spectrosc., 1988, 132, 2, 393, https://doi.org/10.1016/0022-2852(88)90334-7 . [all data]

Bannai and Duxbury, 1994
Bannai, R.A.; Duxbury, G., Fourier-transform infrared spectra of formaldoxime: ν_4, ν_5, ν_6, and ν_8 bands, J. Opt. Soc. Am. B, 1994, 11, 1, 170, https://doi.org/10.1364/JOSAB.11.000170 . [all data]

Duxbury, Percival, et al., 1988
Duxbury, G.; Percival, R.M.; Devoy, D.; Mahmoud, M.R.M., Fourier transform and diode laser spectroscopy of the 10-μm bands of formaldoxime (CH2NOH), J. Mol. Spectrosc., 1988, 132, 2, 380, https://doi.org/10.1016/0022-2852(88)90333-5 . [all data]

Jacox, 1994
Jacox, M.E., Vibrational and electronic energy levels of polyatomic transient molecules, American Chemical Society, Washington, DC, 1994, 464. [all data]

Jacox, 1998
Jacox, M.E., Vibrational and electronic energy levels of polyatomic transient molecules: supplement A, J. Phys. Chem. Ref. Data, 1998, 27, 2, 115-393, https://doi.org/10.1063/1.556017 . [all data]

Levine, 1962
Levine, I.N., The microwave spectrum of formaldoxime, J. Mol. Spectrosc., 1962, 8, 1-6, 276, https://doi.org/10.1016/0022-2852(62)90028-0 . [all data]

Levine, 1963
Levine, I.N., Structure of Formaldoxime, J. Chem. Phys., 1963, 38, 10, 2326, https://doi.org/10.1063/1.1733504 . [all data]

Kaushik and Takagi, 1978
Kaushik, V.K.; Takagi, K., Centrifugal Distortion Effects in the Microwave Rotational Spectrum of Formaldoxime, J. Phys. Soc. Japan, 1978, 45, 6, 1975, https://doi.org/10.1143/JPSJ.45.1975 . [all data]

Klesing and Sutter, 1990
Klesing, A.; Sutter, D.H., Z. Naturforsch., 1990, 45A, 817. [all data]

Notes

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Symbols used in this document:

IE (evaluated) Recommended ionization energy

Δ_rH° Enthalpy of reaction at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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IE (evaluated)	Recommended ionization energy
Δ_rH°	Enthalpy of reaction at standard conditions