Table 1 Comparison between measured and calculated pKcycl values of HMR derivatives.

From: Molecular design strategy of fluorogenic probes based on quantum chemical prediction of intramolecular spirocyclization

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X

Y

Z

R1

R2

Measured pKcycl

Calculated pKcycl

Error

HMRG

O

O

H

H

H

8.1

11.3 (7.9a)

0.2

AMRG

O

NH

H

H

H

6.2

10.1 (6.2a)

0.0

HMTMR

O

O

H

Me

Me

9.5

9.5

0.0

AMTMR

O

NH

H

Me

Me

7.8

8.1

0.3

HMRB

O

O

H

Et

Et

9.2

9.3

0.1

AMRB

O

NH

H

Et

Et

8.2

8.1

0.1

HMSiR

SiMe2

O

H

Me

Me

5.7

6.2

0.5

AMSiR

SiMe2

NH

H

Me

Me

4.2

4.8

0.6

HMDiMeR

O

O

H

H

Me

8.9

9.2

0.3

HMDiEtR

O

O

H

H

Et

9.3

8.8

0.5

HMJR

O

O

H

H

Julolidineb

10.3

10.7

0.4

HMDiMeFR

O

O

F

H

Me

8.2

8.3

0.1

HMDiMeCR

O

O

Cl

H

Me

7.7

7.3

0.4

HMJFR

O

O

F

H

Julolidineb

9.8

9.8

0.0

HMJCR

O

O

Cl

H

Julolidineb

9.1

8.7

0.4

HMSiR620h

SiMe2

O

H

H

Me

5.0

4.8

0.2

HMJSiR

SiMe2

O

H

H

Julolidineb

6.6

7.1

0.4

  1. Measured values are from the literature16,24,27.
  2. aData were calculated with 5 explicit water molecules.
  3. bIn the case of R2 = julolidine, the structure of the compound is as shown on the right.
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