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Dioxetanes are heterocyclic organic compounds which consist of a four-membered ring that contains two oxygen atoms and two carbon atoms. 1,2-Dioxetane is an organic peroxide with the two oxygen atoms adjacent to each other. 1,3-Dioxetane has alternating oxygen and carbon atoms.
Some dioxetanes are responsible for bioluminescence. In the 1960s biochemists came to the conclusion that these compounds had a fleeting existence in fireflies, glow-worms and other luminescent creatures. The instability of these four-membered cyclic peroxides meant that the hypothesis could not be proved. Then in 1968 the first example of a stable dioxetane was made during the course of other research at the University of Alberta in Edmonton. This first example was 3,3,4-trimethyl-1,2-dioxetane prepared as a yellow solution in benzene. When heated to 333 K, it decomposed smoothly rather than explosively as many peroxides do. Moreover, it decomposed to acetone and acetaldehyde with the emission of pale blue light.
The second example of a dioxetane was made shortly after. It was the symmetrical compound 3,3,4,4-tetramethyl-1,2-dioxetane. This could be obtained as pale yellow crystals that sublimed even when kept in the refrigerator. Benzene solutions of this compound also decomposed smoothly with the emission of blue light. By adding compounds that normally fluoresce in UV light the colour of the emitted light could be altered. Because theoretical scientists seek to understand the mechanism of light emission this second example rapidly became the most studied symmetrical compound ever. .The luminescent bangles and necklaces worn at outdoor evening events make use of a dioxetane derivative called dioxetanedione that decomposes to carbon dioxide.
Other dioxetanes are used in clinical analysis where the ability to detect very faint light emission allows chemists to detect very low concentrations of body fluid constituents.
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1,2-dioxetane
Dioxetane
6788-84-7
[RN]
|
LogP: |
ACD/LogP:
-0.62
XLogP:
-0.10
|
# of Rule of 5 Violations: |
0
|
|
ACD/LogD (pH 5.5): |
-0.62
|
ACD/LogD (pH 7.4): |
-0.62
|
|
ACD/BCF (pH 5.5): |
1
|
ACD/BCF (pH 7.4): |
1
|
|
ACD/KOC (pH 5.5): |
10.95
|
ACD/KOC (pH 7.4): |
10.95
|
|
#H bond acceptors: |
2
|
#H bond donors: |
0
|
|
#Freely Rotating Bonds: |
0
|
Polar Surface Area: |
18.46
Å2
|
|
Index of Refraction: |
1.384
|
Molar Refractivity: |
12.43
cm3
|
|
Molar Volume: |
53
cm3
|
Polarizability: |
4.92
10-24cm3
|
|
Surface Tension: |
35.2
dyne/cm
|
Density: |
1.131
g/cm3
|
|
Flash Point: |
°C
|
Enthalpy of Vaporization: |
22.49
kJ/mol
|
|
Boiling Point: |
°C at 760 mmHg
|
Vapour Pressure: |
3220
mmHg at 25°C
|
Log Octanol-Water Partition Coef (SRC):
Log Kow (KOWWIN v1.67 estimate) = 0.61
Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
Boiling Pt (deg C): 48.39 (Adapted Stein & Brown method)
Melting Pt (deg C): -87.23 (Mean or Weighted MP)
VP(mm Hg,25 deg C): 325 (Mean VP of Antoine & Grain methods)
Water Solubility Estimate from Log Kow (WSKOW v1.41):
Water Solubility at 25 deg C (mg/L): 4.125e+004
log Kow used: 0.61 (estimated)
no-melting pt equation used
Water Sol Estimate from Fragments:
Wat Sol (v1.01 est) = 23232 mg/L
ECOSAR Class Program (ECOSAR v0.99h):
Class(es) found:
Peroxy Acids
Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
Bond Method : 9.63E-004 atm-m3/mole
Group Method: Incomplete
Henrys LC [VP/WSol estimate using EPI values]: 6.225E-004 atm-m3/mole
Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
Log Kow used: 0.61 (KowWin est)
Log Kaw used: -1.405 (HenryWin est)
Log Koa (KOAWIN v1.10 estimate): 2.015
Log Koa (experimental database): None
Probability of Rapid Biodegradation (BIOWIN v4.10):
Biowin1 (Linear Model) : 0.7190
Biowin2 (Non-Linear Model) : 0.8962
Expert Survey Biodegradation Results:
Biowin3 (Ultimate Survey Model): 3.0665 (weeks )
Biowin4 (Primary Survey Model) : 3.7611 (days )
MITI Biodegradation Probability:
Biowin5 (MITI Linear Model) : 0.5729
Biowin6 (MITI Non-Linear Model): 0.7799
Anaerobic Biodegradation Probability:
Biowin7 (Anaerobic Linear Model): 0.5961
Ready Biodegradability Prediction: YES
Hydrocarbon Biodegradation (BioHCwin v1.01):
Structure incompatible with current estimation method!
Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
Vapor pressure (liquid/subcooled): 4.31E+004 Pa (323 mm Hg)
Log Koa (Koawin est ): 2.015
Kp (particle/gas partition coef. (m3/ug)):
Mackay model : 6.97E-011
Octanol/air (Koa) model: 2.54E-011
Fraction sorbed to airborne particulates (phi):
Junge-Pankow model : 2.52E-009
Mackay model : 5.57E-009
Octanol/air (Koa) model: 2.03E-009
Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
Hydroxyl Radicals Reaction:
OVERALL OH Rate Constant = 0.6433 E-12 cm3/molecule-sec
Half-Life = 16.626 Days (12-hr day; 1.5E6 OH/cm3)
Ozone Reaction:
No Ozone Reaction Estimation
Fraction sorbed to airborne particulates (phi): 4.04E-009 (Junge,Mackay)
Note: the sorbed fraction may be resistant to atmospheric oxidation
Soil Adsorption Coefficient (PCKOCWIN v1.66):
Koc : 48.64
Log Koc: 1.687
Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
Rate constants can NOT be estimated for this structure!
Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
Log BCF from regression-based method = 0.500 (BCF = 3.162)
log Kow used: 0.61 (estimated)
Volatilization from Water:
Henry LC: 0.000963 atm-m3/mole (estimated by Bond SAR Method)
Half-Life from Model River: 1.262 hours
Half-Life from Model Lake : 78.74 hours (3.281 days)
Removal In Wastewater Treatment:
Total removal: 30.05 percent
Total biodegradation: 0.07 percent
Total sludge adsorption: 1.33 percent
Total to Air: 28.64 percent
(using 10000 hr Bio P,A,S)
Level III Fugacity Model:
Mass Amount Half-Life Emissions
(percent) (hr) (kg/hr)
Air 39.7 399 1000
Water 44.6 360 1000
Soil 15.6 720 1000
Sediment 0.0846 3.24e+003 0
Persistence Time: 163 hr
Descriptors:
0, 0, 0, 0, 0, 0, 0, 4, 0, 0, 0, 0, 0, 0, 4, 0, 0, 0, 0, 0, 0, 0, 0, 0
| Category | Target | PDB Code | LASSO Score |
| Kinases | TK, thymidine kinase | 1kim | 0.66 |
| Metalloenzymes | ADA, adenosine deaminase | 1stw | 0.04 |
| Nuclear Hormone Receptors | PPARg, peroxisome proliferator activated receptor | 1fm9 | 0.03 |
| Kinases | HSP90, human heat shock protein 90 | 1uy6 | 0.02 |
| Metalloenzymes | PDE5, phosphodiesterase 5 | 1xp0 | 0.02 |
| Other Enzymes | AmpC, AmpC beta-lactamase | 1xgj | 0.02 |
| Other Enzymes | PNP, purine nucleoside phosphorylase | 1b8o | 0.02 |
| Kinases | SRC, tyrosine kinase SRC | 2src | 0.01 |
| Other Enzymes | HMGR, hydroxymethylglutaryl-CoA reductase | 1hw8 | 0.01 |
| Other Enzymes | GPB, glycogen phosphorylase | 1a8i | 0.01 |
| Nuclear Hormone Receptors | MR, mineralocorticoid receptor | 2aa2 | 0.01 |
| Other Enzymes | HIVPR, HIV protease | 1hpx | 0.01 |
| Folate Enzymes | DHFR, dihydrofolate reductase | 3dfr | 0.00 |
| Metalloenzymes | ACE, angiotensin-converting enzyme | 1o86 | 0.00 |
| Nuclear Hormone Receptors | ER, estrogen receptor; agonist | 1l2i | 0.00 |
| Other Enzymes | PARP, poly(ADP-ribose) polymerase | 1efy | 0.00 |
| Other Enzymes | AChE, acetylcholinesterase | 1eve | 0.00 |
| Nuclear Hormone Receptors | PR, progesterone receptor | 1sr7 | 0.00 |
| Kinases | VEGFr2, vascular endothelial growth factor receptor | 1vr2 | 0.00 |
| Kinases | FGFr1, fibroblast growth factor receptor kinase | 1agw | 0.00 |
| Folate Enzymes | GART, glycinamide ribonucleotide transformylase | 1c2t | 0.00 |
| Nuclear Hormone Receptors | AR, androgen receptor | 1xq2 | 0.00 |
| Kinases | PDGFrb, platelet derived growth factor receptor kinase | N/A | 0.00 |
| Nuclear Hormone Receptors | RXRa, retinoic X receptor R | 1mvc | 0.00 |
| Other Enzymes | SAHH, S-adenosyl-homocysteine hydrolase | 1a7a | 0.00 |
| Kinases | CDK2, cyclindependent kinase 2 | 1ckp | 0.00 |
| Other Enzymes | NA, neuraminidase | 1a4g | 0.00 |
| Kinases | P38 MAP, P38 mitogen activated protein | 1kv2 | 0.00 |
| Serine Proteases | FXa, factor Xa | 1f0r | 0.00 |
| Other Enzymes | HIVRT, HIV reverse transcriptase | 1rt1 | 0.00 |
| Metalloenzymes | COMT, catechol O-methyltransferase | 1h1d | 0.00 |
| Other Enzymes | COX-2, cyclooxygenase-2 | 1cx2 | 0.00 |
| Kinases | EGFr, epidermal growth factor receptor | 1m17 | 0.00 |
| Serine Proteases | Thrombin | 1ba8 | 0.00 |
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