2,5-Dimethylfuran
Singlet oxygen

Gollnick, K.; Knutzen-Mies, K.
J. Org. Chem. 56, 4017-4027 (1991)

Reaction: 2,5-Dimethylfuran + 1O2* ® products
Solvent: MeOH

kreact = 1.8 × 108(L mol-1 s-1), T = 286K

Experimental method: Photolysis
Analytical method: oxygen consumption
Data type: Derived from steady state measurements

Photosensitizer = Rose Bengal dianion. used solvent kd = 1.4 × 105 s-1.

Scully, F.E.,Jr.; Hoigne, J.
Chemosphere 16, 681-694 (1987)

Reaction: 2,5-Dimethylfuran + 1O2* ® products
Reference Reaction: Furfuryl alcohol + 1O2* ®
Solvent: H2O

kreact = 8.2 × 108(L mol-1 s-1), kreference = 1.2 × 108(L mol-1 s-1), pH = 7.0, T = 292K

Experimental method: Modulated photolysis
Analytical method: HPLC
Data type: Relative value measured by steady state method
Excitation wavelength: >520 nm

Photosensitizer = Rose Bengal dianion. Added solute 1 × 10-5. [Sensitizer] = 5 × 10-3 (mol L-1). [Indicator] = 5 × 10-5 (mol L-1).

Cottier, L.; Descotes, G.; Nigay, H.; Parron, J.-C.; Gregoire, V.
Bull. Soc. Chim. Fr., 844-850 (1986)

Reaction: 2,5-Dimethylfuran + 1O2* ® products
Reference Reaction: Furfuryl alcohol + 1O2* ®
Solvent: CH3CH2OH

k/kreference = 1.3
T = 293K

Experimental method: Photolysis
Analytical method: oxygen consumption
Data type: Relative value measured by steady state method

Photosensitizer = Rose Bengal dianion. Meas. k/kref = 1.3.

Clennan, E.L.; Mehrsheikh-Mohammadi, M.E.
J. Am. Chem. Soc. 106, 7112-7118 (1984)

Reaction: 2,5-Dimethylfuran + 1O2* ® products and/or physical quenching
Solvent: CH2Cl2

k = 2.6 × 108(L mol-1 s-1)

Experimental method: Photolysis
Analytical method: vis-UV absorption
Data type: Derived from steady state measurements using indicator

Photosensitizer = Mesoporphyrin IX, dimethyl ester; used solvent kd = 1 × 104 s-1; Indicator = 1,3-Diphenylisobenzofuran.

Clennan, E.L.; Mehrsheikh-Mohammadi, M.E.
J. Am. Chem. Soc. 106, 7112-7118 (1984)

Reaction: 2,5-Dimethylfuran + 1O2* ® products and/or physical quenching
Solvent: CH2Cl2

k = 1.3 × 108(L mol-1 s-1)

Experimental method: Photolysis
Analytical method: vis-UV absorption
Data type: Derived from steady state measurements using indicator

Photosensitizer = Indicator = Rubrene; used solvent kd = 1 × 104 s-1; k for indicator = 3.3 × 107 L/(mol·s).

Reszka, K.; Chignell, C.F.
Photochem. Photobiol. 38, 281-291 (1983)

Reaction: 2,5-Dimethylfuran + 1O2* ® products and/or physical quenching
Solvent: EtOH

k = 2.6 × 108(L mol-1 s-1)

Experimental method: Photolysis
Analytical method: oxygen consumption
Data type: Derived from steady state measurements
Excitation wavelength: 309 nm

Photosensitizer = Benoxaprofen; used solvent kd = 8.3 × 104 s-1; Quencher = 1,4-Diazabicyclo[2.2.2]octane, kq = 1.3 × 107 L mol-1 s-1; soln. contg. TEMPO. Use 1,4-Diazabicyclo[2.2.2]octane as quencher.

Fuke, K.; Ueda, M.; Itoh, M.
J. Am. Chem. Soc. 105, 1091-1096 (1983)

Reaction: 2,5-Dimethylfuran + 1O2* ® products and/or physical quenching
Solvent: MeOH

k = 3.8 × 108(L mol-1 s-1)

Experimental method: Flash photolysis
Analytical method: temperature changes
Data type: Absolute value measured directly
Excitation wavelength: 520 nm nm

Photosensitizer = Erythrosin dianion.

Manring, L.E.; Foote, C.S.
J. Phys. Chem. 86, 1257-1259 (1982)

Reaction: 2,5-Dimethylfuran + 1O2* ® products and/or physical quenching
Reference Reaction: TMPD + 1O2* ®
Solvent: H2O

k = 1.1 × 109(L mol-1 s-1)

Experimental method: Flash photolysis
Analytical method: vis-UV absorption
Data type: Derived from steady state measurements using indicator

Photosensitizer = Erythrosin dianion; used solvent kd = 3.3 × 105 s-1; Indicator = N,N,N',N'-Tetramethyl-p-phenylenediamine.

Fuke, K.; Ueda, M.; Itoh, M.
Chem. Phys. Lett. 76, 372-374 (1980)

Reaction: 2,5-Dimethylfuran + 1O2* ® products and/or physical quenching
Solvent: MeOH

k = 9 × 107(L mol-1 s-1)

Experimental method: Flash photolysis
Analytical method: temperature changes
Data type: Absolute value measured directly

Photosensitizer = Biacetyl. [Indicator] = 1 × 10-2 (mol L-1).

Gorman, A.A.; Lovering, G.; Rodgers, M.A.J.
J. Am. Chem. Soc. 101, 3050-3055 (1979)

Reaction: 2,5-Dimethylfuran + 1O2* ® products and/or physical quenching
Solvent: C6H5CH3

Enthalpy of activation = 0(kJ mol-1), Entropy of activation = 0.0(J K-1 mol-1), Temperature range 223 to 353 K
k = 6.3 × 108(L mol-1 s-1)

Experimental method: Pulse radiolysis
Analytical method: vis-UV absorption
Data type: Absolute value measured directly using indicator

Photosensitizer = Naphthalene; Indicator = 1,3-Diphenylisobenzofuran. [Sensitizer] = 10-2 (mol L-1).

Usui, Y.; Tsukada, M.; Nakamura, H.
Bull. Chem. Soc. Jpn. 51, 379-384 (1978)

Reaction: 2,5-Dimethylfuran + 1O2* ® products and/or physical quenching
Solvent: EtOH

k = 3.8 × 108(L mol-1 s-1), b = 2.2 × 10-4(mol L-1), T = 298K

Experimental method: Photolysis
Analytical method: vis-UV absorption
Data type: Derived from steady state measurements

Photosensitizer = Methylene Blue; used solvent kd = 8.3 × 104 s-1.

Delmelle, M.
Photochem. Photobiol. 27, 731-734 (1978)

Reaction: 2,5-Dimethylfuran + 1O2* ® products and/or physical quenching
Solvent: EtOH

b = 1.5 × 10-4(mol L-1)

Experimental method: Photolysis
Analytical method: vis-UV absorption
Data type: Derived from steady state measurements

Photosensitizer = Methylene Blue; meas. kd/k = 1.5 × 10-4 mol/L.

Delmelle, M.
Photochem. Photobiol. 27, 731-734 (1978)

Reaction: 2,5-Dimethylfuran + 1O2* ® products and/or physical quenching
Solvent: EtOH

b = 1.6 × 10-4(mol L-1)

Experimental method: Photolysis
Analytical method: vis-UV absorption
Data type: Derived from steady state measurements

Photosensitizer = (all-E)-Retinal. meas. kd/k = 1.6 × 10-4 mol/L.

Held, A.M.; Halko, D.J.; Hurst, J.K.
J. Am. Chem. Soc. 100, 5732-5740 (1978)

Reaction: 2,5-Dimethylfuran + 1O2* ® products and/or physical quenching
Solvent: H2O

b = 5.5 × 10-4(mol L-1), T = 298K

Experimental method: Chemical reaction
Analytical method: oxygen consumption
Data type: Derived from steady state measurements

meas. kd/k = 5.5 × 10-4 mol/L. 1O2* from H2O2/NaOCl.

Usui, Y.; Tsukada, M.; Nakamura, H.
Bull. Chem. Soc. Jpn. 51, 379-384 (1978)

Reaction: 2,5-Dimethylfuran + 1O2* ® products and/or physical quenching
Solvent: H2O

k = 1.6 × 109(L mol-1 s-1), b = 3.2 × 10-4(mol L-1), T = 298K

Experimental method: Photolysis
Analytical method: vis-UV absorption
Data type: Derived from steady state measurements

Photosensitizer = Methylene Blue; used solvent kd = 5.0 × 105 s-1.

Usui, Y.; Tsukada, M.; Nakamura, H.
Bull. Chem. Soc. Jpn. 51, 379-384 (1978)

Reaction: 2,5-Dimethylfuran + 1O2* ® products and/or physical quenching
Solvent: MeOH

k = 3.9 × 108(L mol-1 s-1), b = 2.8 × 10-4(mol L-1), T = 298K

Experimental method: Photolysis
Analytical method: vis-UV absorption
Data type: Derived from steady state measurements

Photosensitizer = Methylene Blue; used solvent kd = 1.1 × 105 s-1.

Lightner, D.A.; Pak, C.-S.
J. Org. Chem. 40, 2724-2728 (1975)

Reaction: 2,5-Dimethylfuran + 1O2* ® products and/or physical quenching
Solvent: (CH3)2CO

k = 2.1 × 108(L mol-1 s-1), b = 1.8 × 10-4(mol L-1)

Experimental method: Photolysis
Analytical method: oxygen consumption
Data type: Derived from steady state measurements

Photosensitizer = Methylene Blue; used solvent kd = 3.8 × 104 s-1.

Lightner, D.A.; Pak, C.-S.
J. Org. Chem. 40, 2724-2728 (1975)

Reaction: 2,5-Dimethylfuran + 1O2* ® products and/or physical quenching
Solvent: MeOH

k = 1.4 × 108(L mol-1 s-1), b = 1.0 × 10-3(mol L-1)

Experimental method: Photolysis
Analytical method: oxygen consumption
Data type: Derived from steady state measurements

Photosensitizer = Rose Bengal dianion. used solvent kd = 1.4 × 105 s-1.

Usui, Y.; Kamogawa, K.
Photochem. Photobiol. 19, 245-247 (1974)

Reaction: 2,5-Dimethylfuran + 1O2* ® products and/or physical quenching
Solvent: H2O

k = 1.6 × 109(L mol-1 s-1), b = 3.1 × 10-4(mol L-1), T = 298K

Experimental method: Photolysis
Analytical method: vis-UV absorption
Data type: Derived from steady state measurements

Photosensitizer = Methylene Blue; used solvent kd = 5.0 × 105 s-1.

Dalle, J.P.; Magous, R.; Mousseron-Canet, M.
Photochem. Photobiol. 15, 411-419 (1972)

Reaction: 2,5-Dimethylfuran + 1O2* ® products and/or physical quenching
Reference Reaction: 1-Cyclohexylamino-4-phenylaminobenzene + 1O2* ®
Solvent: EtOH

b = 3.3 × 10-3(mol L-1), T = 273K

Experimental method: Photolysis
Analytical method: oxygen consumption
Data type: Derived from steady state measurements

Photosensitizer = Methylene Blue; meas. kd/k = 3.3 × 10-3 mol/L.

Merkel, P.B.; Kearns, D.R.
J. Am. Chem. Soc. 94, 7244-7253 (1972)

Reaction: 2,5-Dimethylfuran + 1O2* ® products and/or physical quenching
Solvent: MeOH

k = 4 × 108(L mol-1 s-1)

Experimental method: Flash photolysis
Analytical method: vis-UV absorption
Data type: Absolute value measured directly using indicator
Excitation wavelength: 694 nm

Photosensitizer = Methylene Blue; Indicator = 1,3-Diphenylisobenzofuran.

Young, R.H.; Wehrly, K.; Martin, R.L.
J. Am. Chem. Soc. 93, 5774-5779 (1971)

Reaction: 2,5-Dimethylfuran + 1O2* ® products and/or physical quenching
Solvent: MeOH

b = 2.8 × 10-4(mol L-1)

Experimental method: Photolysis
Analytical method: vis-UV emission
Data type: Derived from steady state measurements using indicator

Photosensitizer = Methylene Blue; Indicator = 1,3-Diphenylisobenzofuran; meas. kd/k = 2.8 × 10-4 mol/L. see also [72YOU/MAR].

Young, R.H.; Wehrly, K.; Martin, R.L.
J. Am. Chem. Soc. 93, 5774-5779 (1971)

Reaction: 2,5-Dimethylfuran + 1O2* ® products and/or physical quenching
Solvent: MeOH, 50%, tert-BuOH, 50%

b = 1.6 × 10-4(mol L-1)

Experimental method: Photolysis
Analytical method: vis-UV emission
Data type: Derived from steady state measurements using indicator

Photosensitizer = Rose Bengal dianion; Indicator = 1,3-Diphenylisobenzofuran. meas. kd/k = 1.6 × 10-4 mol/L.

Koch, E.
Tetrahedron 24, 6295-6318 (1968)

Reaction: 2,5-Dimethylfuran + 1O2* ® products and/or physical quenching
Solvent: MeOH

Activation energy = 4.2(kJ mol-1)
b ~ 2 × 10-4(mol L-1), T = 293K

Experimental method: Photolysis
Analytical method: oxygen consumption
Data type: Derived from steady state measurements

Photosensitizer = Rose Bengal dianion. meas. kd/k = ~2 × 10-4 mol/L.

Higgins, R.; Foote, C.S.; Cheng, H.
Adv. Chem. 77, 102-117 (1968)

Reaction: 2,5-Dimethylfuran + 1O2* ® products
Reference Reaction: (CH3)2C=C(CH3)2 + 1O2* ®
Solvent: MeOH, 50%, tert-BuOH, 50%

k/kreference = 2.4
T = 303K

Experimental method: Photolysis
Analytical method: gas chromatography
Data type: Relative value measured by steady state method

Photosensitizer = Rose Bengal dianion. Meas. k/kref = 2.4.

Higgins, R.; Foote, C.S.; Cheng, H.
Adv. Chem. 77, 102-117 (1968)

Reaction: 2,5-Dimethylfuran + 1O2* ® products
Reference Reaction: (CH3)2C=C(CH3)2 + 1O2* ®
Solvent: MeOH, 50%, tert-BuOH, 50%

k/kreference = 1.5
T = 303K

Experimental method: Chemical reaction
Analytical method: gas chromatography
Data type: Relative value measured by steady state method

1O2* from H2O2/Ca(OCl)2. Meas. k/kref = 1.5.

Higgins, R.; Foote, C.S.; Cheng, H.
Adv. Chem. 77, 102-117 (1968)

Reaction: 2,5-Dimethylfuran + 1O2* ® products
Reference Reaction: (CH3)2C=C(CH3)2 + 1O2* ®
Solvent: MeOH, 50%, tert-BuOH, 50%

k/kreference = 5.2
T = 303K

Experimental method: Chemical reaction
Analytical method: gas chromatography
Data type: Relative value measured by steady state method

1O2* from H2O2/NaOCl. Meas. k/kref = 5.2.

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