On Sulphonfluoresceïn and Some of Its Derivatives — John Shaqi
On Sulphonfluoresceïn and Some of Its DerivativesHayes, C. W. (Charles Willard)
Science
On Sulphonfluoresceïn and Some of Its Derivatives
Hayes, C. W. (Charles Willard)
Sulfonefluorescein; Thesis (Ph. D.)
These analyses show with but little doubt that the substance has the
composition indicated above i.e. C_{19}H_{12}O_{6}S+2H_{2}O. The
reaction therefore which takes place between ortho-sulpho benzoic
acid and resorcin from its analogy to that taking place between
phthalic anhydride and resorcin may be represented thus, as shown by
Baeyer in his second paper (Ann. 202. S. 43)
Representing the formation of the anhydride as the first action.
COOH CO
╱ ╱ ╲
C_{6}H_{4} = C_{6}H_{4} O + H_{2}O
\ ╲ ╱
SO_{2}OH(o) SO_{2}
and the action of resorcin on this anhydride thus.
CO OH
╱ ╲ ╱
C_{6}H_{4} O + 2C_{6}H_{4}
╲ ╱ ╲
SO_{2} OH (m)
O
╱ ╲
(HO)H_{4}C_{6} C_{6}H_{4}(OH)
╲ ╱
= C + 2H_{2}O
╱ ╲
C_{6}H_{4} O
╲ ╱
SO_{2}
The substance thus formed would naturally receive the name
Sulphonfluoresceïn from its analogy with Fluoresceïn.
┌─
│ OH
│ ╱
│ C_{6}H_{3}
│ ╲
│ O
│ ╱
C ─┤ C_{6}H_{3}
│ ╲
│ OH
│
│ C_{6}H_{4}SO_{2}
│ ╱
│ O
└─
Sulphonfluoresceïn.
┌─
│ OH
│ ╱
│ C_{6}H_{3}
│ ╲
│ O
│ ╱
C ─┤ C_{6}H_{3}
│ ╲
│ OH
│
│ C_{6}H_{4}CO
│ ╱
│ O
└─
Fluoresceïn.
Properties of S.fluoresceïn.
This compound shows a marked similarity to the fluoresceïn described
by Baeyer as would naturally be expected from its great similarity of
composition and constitution, but it also shows decided differences
which may be attributed to the replacement of CO by SO_{2}.
Dissolved in water it shows a weak green fluorescence which in
alkaline solution becomes much deeper but not by any means so strong
as that of fluoresceïn. The dilute alkaline solution by transmitted
light is almost perfectly colorless and by reflected light a clear
green. Unlike fluoresceïn it is extremely soluble in water, about
one part in two or three of hot and five or six of cold water. It
is also soluble in absolute alcohol forming a yellow solution with
weak fluorescence. It is soluble with difficulty in ether but when in
solution is deposited only on evaporating to a small volume.
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