Solvent
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Norsk bokml constant measures the solvent's tendency to partly cancel the field strength of the electric field of a charged
Norsk nynorsk particle immersed in it. This reduction is then compared to the field strength of the charged particle in a
Polski vacuum.[4] Heuristically, the dielectric constant of a solvent can be thought of as its ability to reduce the solute's
Portugus effective internal charge. Generally, the dielectric constant of a solvent is an acceptable predictor of the
Romn solvent's ability to dissolve common ionic compounds, such as salts.
Scots
Other polarity scales [ edit ]
Sicilianu
Simple English Dielectric constants are not the only measure of polarity. Because solvents are used by chemists to carry out
Slovenina chemical reactions or observe chemical and biological phenomena, more specific measures of polarity are
Slovenina required. Most of these measures are sensitive to chemical context.
Soomaaliga
/ srpski The Grunwald Winstein mY scale measures polarity in terms of solvent influence on buildup of positive charge
Srpskohrvatski / of a solute during a chemical reaction.
Suomi Kosower's Z scale measures polarity in terms of the influence of the solvent on UV-absorption maxima of a salt,
Svenska usually pyridinium iodide or the pyridinium zwitterion.[5]
Donor number and donor acceptor scale measures polarity in terms of how a solvent interacts with specific
substances, like a strong Lewis acid or a strong Lewis base.[6]
Trke The Hildebrand parameter is the square root of cohesive energy density. It can be used with nonpolar
Ting Vit Reichardt's dye, a solvatochromic dye that changes color in response to polarity, gives a scale of ET(30)
values. ET is the transition energy between the ground state and the lowest excited state in kcal/mol, and (30)
identifies the dye. Another, roughly correlated scale (ET(33)) can be defined with Nile red.
Edit links
The polarity, dipole moment, polarizability and hydrogen bonding of a solvent determines what type of
compounds it is able to dissolve and with what other solvents or liquid compounds it is miscible. Generally, polar
solvents dissolve polar compounds best and non-polar solvents dissolve non-polar compounds best: "like
dissolves like". Strongly polar compounds like sugars (e.g., sucrose) or ionic compounds, like inorganic salts
(e.g., table salt) dissolve only in very polar solvents like water, while strongly non-polar compounds like oils or
waxes dissolve only in very non-polar organic solvents like hexane. Similarly, water and hexane (or vinegar and
vegetable oil) are not miscible with each other and will quickly separate into two layers even after being shaken
well.
Polarity can be separated to different contributions. For example, the Kamlet-Taft parameters are
dipolarity/polarizability (*), hydrogen-bonding acidity () and hydrogen-bonding basicity (). These can be
calculated from the wavelength shifts of 36 different solvatochromic dyes in the solvent, usually including
Reichardt's dye, nitroaniline and diethylnitroaniline. Another option, Hansen's parameters, separate the
cohesive energy density into dispersion, polar and hydrogen bonding contributions.
0.626
Pentane CH3-CH2-CH2-CH2-CH3 36 C 1.84 0.00 D
g/ml
0.751
Cyclopentane 40 C 1.97 0.00 D
g/ml
C5H10
0.655
Hexane CH3-CH2-CH2-CH2-CH2-CH3 69 C 1.88 0.00 D
g/ml
0.779
Cyclohexane 81 C 2.02 0.00 D
g/ml
C6H12
0.879
Benzene 80 C 2.3 0.00 D
g/ml
0.867
Toluene C6H5-CH3 111 C 2.38 0.36 D
g/ml
1.033
1,4-Dioxane 101 C 2.3 0.45 D
g/ml
/-CH2-CH2-O-CH2-CH2-O-\
( )
1.498
Chloroform CHCl3 61 C 4.81 1.04 D
g/ml
0.713
Diethyl ether CH3-CH2-O-CH2-CH3 35 C 4.3 1.15 D
g/ml
Dichloromethane 1.3266
CH2Cl2 40 C 9.1 1.60 D
(DCM) g/ml
Tetrahydrofuran 0.886
66 C 7.5 1.75 D
(THF) g/ml
/-CH2-CH2-O-CH2-CH2-\
( )
0.894
Ethyl acetate 77 C 6.02 1.78 D
g/ml
CH3-C(=O)-O-CH2-CH3
0.786
Acetone 56 C 21 2.88 D
g/ml
CH3-C(=O)-CH3
Dimethylformamide 0.944
153 C 38 3.82 D
(DMF) g/ml
H-C(=O)N(CH3)2
0.786
Acetonitrile (MeCN) CH3-CN 82 C 37.5 3.92 D
g/ml
100 1.1371
Nitromethane CH3-NO2 35.87 3.56 D
103 C g/ml
Propylene 1.205
C4H6O3 240 C 64.0 4.9 D
carbonate g/ml
1.21
Formic acid 101 C 58 1.41 D
g/ml
H-C(=O)OH
0.810
n-Butanol CH3-CH2-CH2-CH2-OH 118 C 18 1.63 D
g/ml
0.785
Isopropanol (IPA) 82 C 18 1.66 D
g/ml
CH3-CH(-OH)-CH3
0.803
n-Propanol CH3-CH2-CH2-OH 97 C 20 1.68 D
g/ml
0.789
Ethanol CH3-CH2-OH 79 C 24.55 1.69 D
g/ml
0.791
Methanol CH3-OH 65 C 33 1.70 D
g/ml
1.049
Acetic acid 118 C 6.2 1.74 D
g/ml
CH3-C(=O)OH
1.000
Water 100 C 80 1.85 D
g/ml
CH3-CH2-CH2-CH2-CH2-
Hexane 14.9 0.0 0.0
CH3
Benzene C6H6 18.4 0.0 2.0
Toluene C6H5-CH3 18.0 1.4 2.0
Diethyl ether CH3CH2-O-CH2-CH3 14.5 2.9 4.6
Chloroform CHCl3 17.8 3.1 5.7
1,4-Dioxane /-CH2-CH2-O-CH2-CH2-O-\ 17.5 1.8 9.0
Density [ edit ]
Most organic solvents have a lower density than water, which means they are lighter and will form a separate
layer on top of water. An important exception: most of the halogenated solvents like dichloromethane or
chloroform will sink to the bottom of a container, leaving water as the top layer. This is important to remember
when partitioning compounds between solvents and water in a separatory funnel during chemical syntheses.
Often, specific gravity is cited in place of density. Specific gravity is defined as the density of the solvent divided
by the density of water at the same temperature. As such, specific gravity is a unitless value. It readily
communicates whether a water-insoluble solvent will float (SG < 1.0) or sink (SG > 1.0) when mixed with water.
Fire [ edit ]
Most organic solvents are flammable or highly flammable, depending on their volatility. Exceptions are some
chlorinated solvents like dichloromethane and chloroform. Mixtures of solvent vapors and air can explode.
Solvent vapors are heavier than air; they will sink to the bottom and can travel large distances nearly undiluted.
Solvent vapors can also be found in supposedly empty drums and cans, posing a flash fire hazard; hence
empty containers of volatile solvents should be stored open and upside down.
Both diethyl ether and carbon disulfide have exceptionally low autoignition temperatures which increase greatly
the fire risk associated with these solvents. The autoignition temperature of carbon disulfide is below 100 C
(212 F), so objects such as steam pipes, light bulbs, hotplates and recently extinguished bunsen burners are
able to ignite its vapours.
References [ edit ]
1. ^ Tinoco, Ignacio; Sauer, Kenneth and Wang, James C. (2002) Physical Chemistry Prentice Hall p. 134 ISBN 0-13-
026607-8
2. ^ Lowery and Richardson, pp. 181183
3. ^ Malmberg, C. G.; Maryott, A. A. (January 1956). "Dielectric Constant of Water from 0 to 100C" (PDF).
Journal of Research of the National Bureau of Standards. 56 (1): 1. doi:10.6028/jres.056.001 . Retrieved 27 June
2014.
4. ^ a b Lowery and Richardson, p. 177.
5. ^ Kosower, E.M. (1969) "An introduction to Physical Organic Chemistry" Wiley: New York, p. 293
6. ^ Gutmann, V. (1976). "Solvent effects on the reactivities of organometallic compounds". Coord. Chem. Rev. 18
(2): 225. doi:10.1016/S0010-8545(00)82045-7 .
7. ^ Lowery and Richardson, p. 183.
8. ^ a b Solvent Properties Boiling Point . Xydatasource.com. Retrieved on 2013-01-26.
9. ^ Dielectric Constant . Macro.lsu.edu. Retrieved on 2013-01-26.
10. ^ a b Abbott, Steven and Hansen, Charles M. (2008) Hansen Hansen Solubility Parameters in Practice , ISBN 0-
9551220-2-3
11. ^ a b Hansen, Charles M. (2007) Hansen solubility parameters: a user's handbook CRC Press, ISBN 0-8493-
7248-8
12. ^ Selected solvent properties Specific Gravity . Xydatasource.com. Retrieved on 2013-01-26.
13. ^ U.S. Department of Labor > Occupational Safety & Health Administration > Solvents . osha.gov
14. ^ Hung, Tawny; Dewitt, Christopher R.; Martz, Walter; Schreiber, William; Holmes, Daniel Thomas (July 2010).
"Fomepizole fails to prevent progression of acidosis in 2-Butoxyethanol and ethanol coingestion". Clinical
Toxicology. 48 (6): 569571. doi:10.3109/15563650.2010.492350 . PMID 20560787 .
15. ^ Lundberg I, Gustavsson A, Hgberg M, Nise G (1992). "Diagnoses of alcohol abuse and other neuropsychiatric
disorders among house painters compared with house carpenters" . Br J Ind Med. 49 (6): 40915.
doi:10.1136/oem.49.6.409 . PMC 1012122 . PMID 1606027 .
16. ^ Raitta, C; Husman, K; Tossavainen, A (1976). "Lens changes in car painters exposed to a mixture of organic
solvents". Albrecht von Graefes Archiv fr klinische und experimentelle Ophthalmologie. 200 (2): 14956.
doi:10.1007/bf00414364 . PMID 1086605 .
17. ^ Mergler, D; Blain, L; Lagac, J. P. (1987). "Solvent related colour vision loss: An indicator of neural damage?".
International archives of occupational and environmental health. 59 (4): 31321. doi:10.1007/bf00405275 .
PMID 3497110 .
Bibliography [ edit ]
Lowery, T.H. and Richardson, K.S., Mechanism and Theory in Organic Chemistry, Harper Collins Publishers
3rd ed. 1987 ISBN 0-06-364044-9
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